>So now what should I do with all this extra disposable income i’ll have moving forward?

I'd say try out a new perspective: no income is "disposable", it just gets different jobs of varying importance. As a responsible adult, you get to set your own priorities. Though there are guidelines to help out.

The wiki has its Prime directive that gives a good roadmap. The top part of the flowchart there sets you up with a good financial foundation:

• Set up a budget where you plan your outgoing money to be <= your incoming money. This will likely take some time to nail down, especially as things shift while you progress through the next steps.
• As part of that budget, you allocate income to your mandatory expenses (rent, transportation, minimum debt payments)
• Contribute enough to your employer's retirement plan (if any) to maximize the amount of match (if any) you can get from them.
• Pay off high-interest debts (especially credit card balances) as fast as your income allows
• Build an emergency fund to protect you against unexpected events
• Save 15% of your income towards your eventual retirement.

Once you've nailed down those half-dozen things, you have a bit of flexibility on how to move forward. You can (within your budget) expand your lifestyle. You can save for a big future purchase (new car, first home). You can aim for early retirement. Or any mix of those that matches your goals / values.

>Do I have to wait until next year to do convert over?

You are allowed by the IRS to do as many Roth conversions as you want during a given year, and for any amount individually / in total. You only report once for the total amount for the year on your 2023 tax return (filed next year), if that's what you came across?

I suppose whatever particular brokerage you have your IRA with could be more restrictive, but I can't think of any reason they would be.

>If I wait until next year, can it still fall under the 2023 tax year given it will be 2024 next year.

There are two pieces you're dealing with, with separate reporting requirements. First is your contributions, which go onto the tax return for the year you contributed for (even if the calendar date of the deposit is in the first few months of the following year). The conversion gets reported on the return for whichever calendar year you executed it.

>Additionally, does the interest earned on my current balance count towards the 6500 max 2023 amount.

No. Only new money going from your regular bank account into the IRA counts towards that max. Once contributed (which only counts what you're putting into the Traditional IRA, not the later conversion), the money you shift around between IRAs no longer matters for that limit. So any interest/growth that happens inside the IRA doesn't count against your $6500 allowed. However, if it happens before you convert into your Roth, that would result in some of what you convert being taxable (whatever interest accrued).

Exactly. It's a bit more preparation you'd have to do now (setting up that link before you can complete the rollover), but that'll keep your bank information on record for future use.

There is one other limitation I forgot to mention. The IRS only allows you to do one indirect HSA rollover every twelve months. So if you happen to need to do another rollover before January 2024, you'd have to make sure that future one is done as a "direct" transfer between the HSA providers. I think that twelve month period is based on the date of the withdrawal from the sending HSA, but I'm not 100% sure.

Those just appear to be your options for moving money into the HSA. Whether that deposit gets marked as a rollover or a regular contribution would be a different selection. Unless you've already told HealthEquity you're doing a rollover and that was the next step?

Long-term, having a verified bank account "linked" with your HSA is handy, which appears to be option 2. That simplifies your ability to get money into / out of the HSA as needed. Usually you provide your checking account info, the HSA does a "test" deposit / withdrawal (sometimes multiples) of some small amount. Once those transactions shows up at your bank you come back to the HSA and provide the amount they sent to confirm all the info was correct.

>Can i deposit it in my bank account and then send money to health equity? Thank you

Yes. Two things to be aware of:

1. You have 60 days to complete this "indirect rollover". Take longer than that and the withdrawal will be counted as a distribution, triggering tax/penalty if you don't have sufficient medical expenses to balance against it.
2. When doing the deposit, your new HSA should allow you to mark it as a "rollover deposit" (or some similar term). This would cause this deposit to not count towards your annual contribution limit. And being reported as that allows you to align this rollover deposit with the withdrawal from your old HSA.

Your new HSA may allow you to do that rollover deposit online with an electronic fund transfer.

Personally, I'd hang onto it in something safe enough for a timeline of a year or two (so HYSA or maybe I-bonds). The student loan forgiveness has gotten a few setbacks, and things are dragging out. There's even a chance that it might get killed altogether. My crystal ball is on the fritz, so I couldn't say how high that chance is, but that possibility is worth keeping in mind. Keeping this earmarked to get put back towards your loan could be your safest bet.

>Am I legally allowed to contribute up to $7300 even though we are not married, but are living together as domestic partners?

Yes (though see my last paragraph below). The only criteria for allowing $7300 of contributions is that the owner of the HSA is covered by a "family" plan. What other individuals are being covered doesn't matter for purposes of determining your HSA contribution limit. It can be you + domestic partner, you + spouse, you as a single parent + child, whatever.

>She is self employed. Can we both contribute up to $7300 in our separate HSA accounts?

Oddly enough, yes, as long as each individual's HSA contribution stays under the $7300 limit. This is a quirky loophole around the HSA contribution limit rules, which also crops up in situations of parents with their adult (non-dependent) children covered by the same family insurance plan.

On your tax return, you would indicate whether you have individual or family coverage. If it's family, then your HSA contributions can go up to $7300. On your partner's separately filed tax return, they'd also indicate family coverage and also be allowed up to $7300 in contributions into their HSA.

This loophole closes for couples who file as married (either jointly or separately). That situation explicitly limits the couple to $7300 in total going into HSAs owned by either spouse, though AFAIK it doesn't matter which individual's HSA gets what share of that total.

As one last bit, technically your contribution limit gets pro-rated based on each month's HDHP coverage status. So if you switched coverage in the middle of 2022, you'd have some months that use the "individual HDHP" amount (1/12th of the $3650 individual max per month of coverage) and some as "family". You partner would have (I assume) some months of no HDHP coverage (so $0 added to the limit) + some months of "family" coverage. However, there's a "last month rule" exception to that, which you may want to check into to see if that can safely apply. If used, you each would use your coverage status as of December 1 2022 to determine your allowed 2022 max.

Based on your other replies, the ESPP gives you a 15% discount with a six-month lookback, and no holding period. So yes, this is practically guaranteed return of roughly 15%, even after taxes. As long as you can cashflow your expenses to account for the money going into the ESPP instead of your bank account, then this is a good way to get extra benefit from your employer.

The worst case scenario would be from the fact that there's usually a small window between when the buy executes and your subsequent sale, since it can take a few days for everything to settle. So it's possible that during that window your employer's stock price plummets below even your discounted price. But unless it's an extremely volatile stock that's generally not likely.

The best case scenario is that the stock price rises dramatically between Jan 1 and Jun 30. You buy at the Jan 1 price (minus discount) and sell at the July 1-3 price and pocket the profit.

One thing to be aware of is how you'll need to report this on your tax return for purposes of properly calculating short-term capital gains. When you do an immediate sale, the "discount portion" of the transaction gets reported on your W-2 as part of your compensation. Using that "buy stock worth $100 for $85" example, your employer essentially pays you that $15 difference, it just went straight into the stock purchase instead of your paycheck. The IRS taxes that $15 along with the rest of your pay.

But on the 1099-B you get from the brokerage, the "basis" of those shares will be the discounted $85 price that you paid. If you use that number as-is, then it'll look like you realized a $15 capital gain, which the IRS will tax. But that $15 was already reported on your W-2, resulting in you double taxing yourself.

The fix is to do a "basis adjustment" to bring the stock's basis up to the fair market value as of the date of purchase, basically adding back the dollars already reported on your W-2 so they don't get included again when calculating gains. There are steps on the Schedule D to do that. Most tax prep software is getting better about walking you through the adjustment if you tell it that these shares were obtained through an ESPP.

In the RSU agreements I've seen, what you're "really" being offered is some number of shares. The dollar amount that gets quoted is based off of the stock price at that time, but that's not usually guaranteed. So if it was trading at $100 / share when you were hired, they were agreeing to give you 1000 shares. If the company stock goes down to $75, you should still be owed those 1000 shares, vesting 250 of them after one year then more as time goes on.

The fact the company went private can certainly change things. One the one hand, your RSU agreement may stand, but you just receive shares in a non-public company. That usually makes valuing them more ambiguous, and can limit who is available to buy them from you. Or there might've been some "buyout" of outstanding shares (vested or unvested), but you should've gotten some communication about that. Or maybe going private involved invalidating any RSU agreements, which would definitely be a dick move, but might be allowed.

What's the actual pay date for your check? I'm paid every other Friday, and my employer's payroll system will show my pay stub a day or two before that, it usually shows up as a "pending" transaction at my bank on Thursday, and doesn't actually get added to my account balance until Friday. Sometimes that "pending" state is skipped and the transaction just pops up completed on Friday.

I haven't used Capital One, but it's possible they received the transaction this morning, but are just being slow to update your account. I'd give it at least a day before starting to worry, these things might be getting batched up into one in the morning (for anything received overnight) and one in the evening (for stuff received after the morning batch was processed). Could just be a timing thing.

Is this your first paycheck at a new job? That can sometimes involve extra validation (employer making sure you gave them a valid account), which can slow things down. That usually smooths out for future deposits.

>The free plan's maximum out of pocket contribution is $8,700, which exceeds $7,500 I see as the $2023 number.
>
>Is the $7,500 max out of pocket a cap or the threshold? Basically, will the play qualify as HDHP?

To count as an HSA eligible HDHP (using 2023's individual coverage thresholds), the plan's out-of-pocket maximum must be lower than $7500. There are also a couple other criteria for HSA eligibility: the plan deductible must be higher than $1500 and the plan cannot cover anything (other than preventative care) prior to meeting that deductible. So if the plan involves co-pays prior to deductible, it won't count as HSA eligible.

In practically all cases, if a plan is HSA eligible then it will say so. If that's not part of the description, it's almost never HSA eligible. So enrolling in that plan means that you would not be allowed to have an HSA, even one you opened independently. Ok, technically you can open one, but you're not eligible to contribute anything into it, which makes it effectively useless.

>If not, should I sign up for the company's FSA, even if it does not roll over unused funds?

Do you have any known (or at least high-likelihood) medical expenses for 2023? If so, then you can enroll in the FSA up to that dollar amount. Think of the tax savings of the FSA as a "discount" on your medical bills. You contribute, say, $1000 into the FSA but your take-home only goes down $800 or so. You can then use the FSA to pay for $1000 of medical costs, saving yourself $200. And that FSA money can be used for your expenses, your wife's, or dependents (if any), even when they're not covered by your insurance plan.

One benefit of an FSA vs. an HSA is that the full dollar amount is available to use immediately at the start of the plan year. You don't have to wait to "fill up" the account from your paycheck deductions. The biggest drawback is the FSA's "use it or lose it", though some will rollover some dollar amount into the next year. Or it'll have a grace period where you can use 2023 FSA dollars for expenses incurred during the first few months of 2024.

Another option would be to find a new bank with a more reliable bill pay. I've used bill pay with my own credit union for over 15 years (maybe creeping up on 20?) and had a problem exactly once. The payment was received by the merchant (credit card) the day after my chosen "deliver by" date. The CU has a "payment guarantee" with their service, so they reimbursed me for the interest + late fee that failure incurred. Sadly, they wouldn't do anything about the following month's card interest (since new charges were no longer in its grace period), but I took what I could get. I have gotten slightly less trusting, so now I set the payments to arrive a business day (or two) prior to their due date to give me a bit more buffer just in case.

I personally prefer to "push" my payments out of my checking account to vendors using my bank's system, rather than allowing vendors to "pull" from my account. Maybe it's overly paranoid, but it gives me a little reassurance against my electric company's payment system having glitch and yanking more out than they're due.

Yes, at that income you get more tax benefit from the DCFSA vs. the dependent care credit.

• The credit saves you 20% on up to $3000 (for a single kid) of your qualified expenses, subtracted from your tax liability.
• The DCFSA lets you put away up $5000, getting your a deduction on your taxable income straight on your paycheck. That contributed money is ignored for federal income tax (24% at your income) + payroll tax (7.6%, though if you or wife are above the social security wage cap, your effective rate may be lower) + state income tax (if applies).

If you have more than one kid, you can benefit from a mix of the two. For two dependents, the cap on "qualified expenses" for the care credit is $6000 (and annoyingly doesn't increase for kids 3+). To prevent "double dipping" on tax savings, any "employer care benefit" you receive (like a DCFSA) is subtracted from that capped amount. With two kids, that ends up leaving up to $1000 of expenses "left over" after taking away the DCFSA that you can still use for the care credit, getting you a $200 tax savings. With a single kid, the $5k DCFSA allowance is > the $3k capped expense, leaving $0 to get any credit against.

As an FYI, the rules for the dependent care credit and DCFSAs were completely different in 2021, but those have expired. There were changes enacted as part of the "American Rescue Plan", but that was a one-year-only thing. So if you're looking up information, make sure that what you're looking at is specifically for 2022 (or for / before 2020, which is what the rules reverted to).