You can see if an ACATS transfer is an option. If you are holding publicly traded stocks, bonds, ETFs, and some mutual funds then everything would transfer without incurring taxes. But proprietary mutual funds might not be able to be transferred or might incur significant transaction fees at your new firm. I think I remember Schwab had an ACATS request form that allowed the user to check what would transfer and what would have to be liquidated before the request was actually submitted. Fidelity might have a similar tool, but otherwise that information should be similar between any pair of institutions. https://www.investopedia.com/terms/a/acat.asp

Yes, TreasuryDirect is for I bonds, that interest rate has been too good to ignore. But don't consider it an essential account everyone must have.

I use Fidelity for my HSA and it's pretty good. I also have my taxable and retirement investments with Schwab and my emergency fund split between Ally and Treasury Direct, so I know how you feel about too many accounts. I think the tax benefit to an HSA is great enough to be worth the extra login information and monitoring demand. You could consider moving your investments from Vanguard to Fidelity, but you will still have to manage additional account statements and tax forms either way.

Banks set up different systems for transferring money between accounts you own or between accounts with different owners. If you opened an account without your mom's name on it, then you will need to use one of the second kinds of transfers. That would be things like Zelle, Venmo, Cash App, etc.

Money exists as a tool to move your life to a better place. If you don't want to buy garbage on Amazon, don't do it, money doesn't actually burn holes in your pocket. If you enjoy the challenge of fixing the lawn mower when it breaks, then it's fine to keep doing that.

What in your life causes you stress today? You might want to think about this for a few weeks or even months. Are you unhappy with your hobbies, social life, physical fitness, etc? Identifying the points in your life that are bringing you stress, unhappiness, and discontent is how you can put unallocated money to good use.

Of course I also acknowledge that money can't fix everything, many of life's problems require significant personal effort to resolve. If your stressor is poor communication with your spouse, you can't just pay money to make you both better communicators, but I would hope having extra money in the budget would make you realize you could afford some sessions with a licensed therapist to guide you, rather than trying to go at it alone.

They did it as an indirect rollover because they sent the check to you personally as opposed to Charles Schwab. If you deposit the check into your CS IRA within 60 days (DO THIS ASAP) and make up the $4400 out of your personal funds then there will be no taxation. If you don't have the cash to do that and only deposit the check, then only the $4400 will be taxed and penalized. You will get a tax document from EJ saying they disbursed money to you, but CS will also report they received money from you and the IRS will know the two cancel each other out.