If you're having that many big expenses that often, it sounds like in some sense they aren't really "unexpected". You're going to have to plan for expenses at that level in your budget, somehow.

This is typically what insurance is for. Perhaps it is time to improve whatever medical insurance you have to cover more (probably at higher premiums), and look into insurance for your pets (which is a thing that exists I hear, although I don't know much about it). Sufficient insurance would at least take the "surprise" out. Earning more to cover the increased insurance premiums isn't really something anyone here can help with -- it sounds like you need to somehow increase your income or reduce your expenses further or both.

A "hobby" and a "part-time job" are two different things. You need to decide which it is. More specifically, what it is right now, this tax year (or last tax year, whichever you're talking about).

Yep, like most things like this, you're far from the first person to have thought of doing this. So, the IRS is prepared for this.

I'm curious what a "contentment creator" does, lol, sounds like an interesting job.

Anyway, the first thing to determine is whether your activity is a "hobby" or a "business". The IRS has various rules for determining that. If it is a "hobby", your taxes will be very simple. If it is a "business" they will be more complex, and probably too much to put into a post here -- there are many websites with articles for self-employed persons.

https://www.irs.gov/newsroom/earning-side-income-is-it-a-hobby-or-a-business

They're both brokerage accounts. For the "Cash Management" account, you would earn interest (currently 2.21%) on cash that is "swept" to various FDIC-insured banks, whereas for the other type of brokerage account you would earn dividends on cash in a Fidelity money market fund (probably SPAXX, currently yielding 3.95%).

You can buy T-Bills in the same manner with either type of brokerage account, so choose whichever one fits any other needs you might have.

The Fidelity Cash Management account is a type of brokerage account. What I was trying to say, in answer to OP's question, is that you cannot have the money deducted directly from your own personal bank account when you buy a T-Bill, you must have the money in your Fidelity brokerage account (whatever type of Fidelity brokerage account it might be).

1. You need a brokerage account. The cash to purchase anything will come from the "settlement fund" (a.k.a. "Core Position") in that brokerage account, which is usually a money market fund of some sort.
2. While logged in to Fidelity, you will go to News & Research > Fixed Income, Bonds & CDs > New Issues > Treasury. There you will see a list of what is available to buy. The money must be in your settlement fund when you hit "Trade" to buy. The "settlement date" listed in the display is when the T-bill will actually start, which will be some number of days later.
3. When the duration you want is available.
4. There is an "Auto roll" option for Treasuries -- I've never used it, so can't comment. Fidelity has a way to build and automatically maintain ladders, but I think that is only for CDs, not for Treasuries.

Assuming you are a beneficiary of the trust, and the trust is now irrevocable (not a living, revocable trust), any distributions from the trust to you are never a "gift", they are a distribution.

Part or all of the distribution may be taxable income to you. The trustee(s) of the trust can decide whether they are distributing principal or income to you, and in what percentage. This will be reflected in the Form K-1 that the trust will have to issue to you. Any of the trust's income (dividends, interest, capital gains) that are distributed to you as part of the distribution can either be taxable to you, or the trust can retain the tax liability and pay the taxes itself -- this is at the discretion of the trustee(s) (unless the trust document says otherwise).

On the other hand, if it is simply a revocable, living trust, then the fact that it is a trust is basically irrelevant. In that case, it is a gift from your mom to you, and the receiver of a gift never owes taxes. Your mom probably wouldn't owe taxes either, just will need to fill out extra forms at tax time to add it to the "lifetime exclusion".

Yes, there are IRA custodians that will allow you create a self-directed IRA that lets you invest in almost anything that is legal for an IRA to invest in (real estate, private equity, private stock, unregistered/private REITs, private notes, etc.). One of the more well-known is "Pacific Premier Trust", but there are many competitors for you to compare and consider.

In my experience such IRA custodians charge much higher fees than "ordinary" IRA custodians, and certainly way more than discount brokerages like Vanguard, Fidelity, etc. That is just the nature of the beast. If you're going to do this, you will have to accept the higher fees as part of it. There will likely be ongoing quarterly and/or annual maintenance fees, and pretty much any action you take in the IRA, including buying the notes you're talking about, will require paying a substantial fee for them to handle the paperwork.

Where I live, the apartment owner is required to make a reasonable effort to re-rent the apartment as soon as possible. If they do re-rent it, then you only have to pay for the period of time during which it was vacant (rather than the full 60 days).

I don't know if other locales, or your locale, have similar requirements.

Of course, it may also be difficult to prove just how hard they really tried to re-rent the place.

Ideally, if you could find another renter that they would accept, that could start sooner than 60 days, that might reduce the amount you have to pay.

Things like this are very much dependent on state law.

First, though, I assume you are not talking about assuming the debt yourself, you are acting as executor of the estate, yes?

I know in California the debtor must make a claim within 1 year of death. However, in addition, the estate is required to notify all known creditors of the death within a certain amount of time, did you do that? Since obviously the estate should have known about this creditor. (But this is California, I don't know about other states).

Most states also require an estate notice to be published in a newspaper.

Assuming the living trust became irrevocable at the time of death (usually the case).

Assuming the stocks were in an account titled in the trust's name before death.

Then, if those assumptions are correct, at the time of death the trust received a stepped-up basis for those stocks owned by the trust.

If at some later time, the trust distributes the stocks in-kind directly to the beneficiaries of the trust, then the beneficiary's basis will be the same as the trust's basis (the stepped-up basis).

If instead, the trust sells the stock and then distributes the proceeds to the beneficiary, then when the trust sells the stock there will be either a loss or gain from the stepped-up basis. At the discretion of the trustee, and depending on what the trust document says about it if anything, the taxable gain or loss can either be declared on the trust's tax return or the tax liability can be transferred to the beneficiary (listed on the K-1 they receive from the trust).

You should confirm this with a CPA familiar with trusts. "Portfolio managers" are not always experts on either trusts or taxes.

Lenders aren't that dumb (well, maybe you could find one who is, who knows). They're looking for recurring real income.