Thanks for taking the time to answer, Rugorak. I'll get on the phone with Vanguard and get all this business under one umbrella. I have to say though, the idea of a Roth seems very appealing as far as the peace of mind of knowing that I won't have to pay taxes later on. And a Roth, from what I understand, can be withdrawn from at any time. I'm still building up my emergency fund at the moment and I don't have the liquid to pay extra taxes right now. So "Traditional" it is.
You can withdraw your contributions at any time. But not any growth. That you have to wait until 59 1/2 (there are a few exceptions but for ease just go with 59 1/2 for growth). And taxes are paid on payroll. So basically if you do a Traditional you will subtract that money from your AGI when you do your taxes. But you would have already paid taxes on them. Since the 401k/403b are pulled out of your paycheck they can adjust your taxes paid right then. Just keep that in mind. Also chances are if the taxes on $5,500 a year are going to make you tight you aren't quite to the $18,000 mark yet on your 401k/403b.
Honestly the taxes shouldn't be a big deal. And if a Roth will get you to be more comfortable with saving go for it. I also liked the Roth for piece of mind. For me the bigger deal is it is kind of a secondary emergency fund. As in I lose my job, get sick, lose health insurance, all at once. I still have 6 months of expenses in a real emergency fund. But the piece of mind knowing I have extra beyond my 6 months is nice. So based on what you have said before I would suggest the following:
1. If you have less than 1 month's expenses in an emergency fund get that much in first (since you are building I am hoping you are past this step).
2. Contribute to 401k/403b up to match. Otherwise you are leaving money on the table.
3. Put excess money into your emergency fund up to 3-6 months of expenses. More if your income is variable or you have some other extenuating circumstances.
4. Pay off high interest debts if you have any.
5. Contribute $5,500 to a Roth (again math wise this is not as good as a Traditional but if the piece of mind helps you it is worth the slightly lower performance).
6. Finish maxing out 401k/403b
7. Once you get here if you still have extra money save/invest in taxable accounts for whatever goals you have. FIRE, a house, whatever.
I have the actual stock (CLS) certificate from when I left the company which was well over 15 years ago. The stock was valued at around $90 a share when it was issued to me. Then March of 2000 happened. Of course, I was ignorant at the time and knew I would have to pay a ton of taxes if I cashed out, so I just put it in the file cabinet and forgot about it.
I'd transfer this to Vanguard as well. Then you can just hang on to it or sell it, but manage it with the rest of your investments. They do not charge for you to add something to your account that you have the certificate for. But if/when you go to sell you'll pay a $7 commission (unless you have over a million invested with them across all your accounts).
