There are two taxable events. First, when your RSUs vest they count as income that you will have to report and pay tax on regardless of if you sell the shares or not.

Then, if you don't sell the shares you'll also owe capital gains tax on any profit between when you eventually sell and the value on the date they vested. Check with the broker to see how they account for the shares - FIFO (first in first out) or LIFO (last in first out) - or possibly, specific ID. You might be able to change that.

https://www.schwab.com/public/eac/resources/articles/rsu_facts.html#:~:text=Taxation,any%20state%20and%20local%20tax.

Try explaining how a CD can lose value to a 90 year old grandparent. As long as you hold it until maturity the current value doesn't matter.

Yuck, an insurance company administering the plan. That spells high fees and sub-optimal investment choices.

I'd be tempted to go with the Vanguard Institutional Index Fund which tracks the S&P 500. According to Vanguard's web site that has an expense ratio of 0.04%. How much is Voya charging?

Yes, that will work. Just make sure the target date fund isn't too expensive (ideally expense ratio as low as possible - anything above ~0.30% I'd be switching for a total stock market index fund which will charge you like 0.04%) and isn't too conservative (low allocation of bonds, or ideally, in your 20s and 30s probably no bonds).

Yes, I like your plan. Forgo the tax savings today and use the Roth accounts so you know in the future what you see in the account is what you get to keep no matter what happens in your financial situation, to the economy overall, to tax rates, etc.

The generally recommended strategy is this:

1. Put enough money into 401k to max out the match you get from your company
2. Then, I'd switch and max out a Roth IRA (if you qualify income wise, else a Traditional IRA). You can put up to 6k into an IRA for 2022.
3. If you still have more money left over that you can afford to save then you can go back and contribute more to the 401k beyond the match

PS - I'd suggest using Roth 401k if your employer offers it (most do nowadays). In both 401k and IRA the name of the game is to invest in simple index funds. Ideally your 401k offers a total stock market index fund like VTSAX. If not, it probably offers an S&P 500 index fund. That is it. You could stick with that allocation for probably the next 20-30 years and be just fine.

PPS - Saving 10% of your income for retirement is a bit low. Aim for at least 15%. Again, the more - especially at a young age - the better.

You are in your late 20s? Are you kidding? I'd be putting every single dollar I could get into my 401k. You buy when markets are down. You don't cut back. Especially in your 20s. The compounding growth power of every $1 you get into your 401k today means it will likely grow to $15-20 by the time you retire. Sure, go ahead and save for a house down payment but not at the expense of stuffing as much as possible into retirement. You'll never be able to make up for these lost compounding years. Waiting just one year (or cutting back) will literally cost you tens of thousands (possibly even 100k).

No worries if you do this. I and millions of other people do. I use my cards 125-150 times per month, always pay the bill in full by the due date, have never had a late payment which shows on my credit (they don't show as late until you are > 30 days late) and my FICO scores are all 800+.

I've got family members whose accounts I manage at Ally, Marcus, Schwab. Been with Ally about 10 years. They haven't screwed up too bad yet.

Wouldn't be overly worried. Account freezes happen at all banks. Lots of people post on r/personalfinance about Wells Fargo doing this. If you are super worried about it open a second savings account at a different bank and split your money so if something happens to Bank A you still have access to money from Bank B. This doesn't even have to be because of account being frozen. It could be computer glitch, ATM network error, bank getting hacked (I'm surprised this doesn't happen much more often) etc. I think about doing this from time-to-time but never have. I suppose one day when it comes back to bite me in the a** I'll wish I had.

Ask if they can advance you some of your pay. Some companies (primarily bigger ones) will also have employee assistance funds which can be used for short-term needs like this.

ACH is perfectly fine. Companies and governments use ACH to transfer tens of millions (even hundreds of millions) of dollars at a time everyday. It is perfectly acceptable for 15k. Only advantage to wire transfer would be speed.

Sounds like you weren't "investing" you were "trading". Investing should mean you put money into something like a total stock market index fund on a regular basis and forget about it for about 30 years. Over time compounding growth means that every $1 you invest today should grow to something like $15-20 by the time you reach retirement. Put another way, every $1 you aren't investing for your future today is costing you $15-20 in lost opportunity that you will never be able to recover.

So the question you should ask yourself is should you spend $5k to go start this business project (not sure what type of business you have in mind, but 5k isn't very much) or would you rather have $75-100k in the future if you invested the money instead?

Yes, most likely a Roth is a good way to go. That way no matter what happens in the future with your economic situation, the economy as a whole, tax rates, etc you know that what you see in the account is what you get to keep. If his employer matches his 401k contributions you already get a little bit of a hedge because the employer match will always go into the pre-tax (traditional) 401k account. So you are likely building up both pre-tax and Roth money.

And you would only be able to deduct if you can claim grandmother as a dependent, which in the scenario you outline you could not. So therefore, no tax benefit.