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No. of Recommendations: 1

As far as I understand it, the 403b, SEP IRA and the ROTH are totally independent, and don't intersect with each other. (if anything intersected, I would think it would be the SEP and the 403b, but you should wait for someone to reply who really knows the inns and outs of this question) I would max out both as much as possible. Someone here should answer this question: Is it possible for you to transfer the stock directly into the ROTH, so you don't have to take the tax hit on it, and then convert it once it is inside? I doubt you can, but it is worth investigating.

In terms of one being better than the other- I don't think there is a huge difference really. However, I would max out both, if possible, because any money saved is going to help you out substantially.

I would definitely roll the old loan with the high interest rate into a new one with a lower interest rate if you go back to school. If you don't go back to school, is it possible to refinance it anyway? It seems like an excessive interest rate for an educational loan.

For your MDT stock, I would diversify it.. it is a huge amount of your savings at the moment. However, considering that you will have to pay capital gains on a lot of it... it makes it more complex.

My personal inclination would be to have you delay school a year, and live extremely frugally and try to knock your debts down for that one year. When you do go to school, keep your costs very low, so you don't keep increasing your debt. I am a little concerned because I have had friends who continually roll into new careers after schooling, thinking the next one will be it, and it just turns into an endless series of increasing debts. not that you will do this! But you should reflect carefully on what is motivating you..

good luck
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