No. of Recommendations: 1
I could rollover these funds directly into the WRS, where I'm guaranteed by law a 5% return per year (and in the past 25 years the fund has averaged a 10.3% return per year).

Do you think your investments in an IRA will guarantee you a 5% return, with the potential of a higher return?

I am correct in assuming that I cannot rollover my 403 (b) into my Roth IRA?

No. You can roll your 403(b) into your Roth IRA. However, it will be considered a conversion in addition to being a rollover, and you will owe taxes, at your marginal rate, on the money you roll over. For $25k at a 25% Federal rate, you would owe an additional $6250 in taxes for 2011. Wisconsin probably would also charge taxes on it.

I would like to keep contributing to whatever type of vehicle I choose, as my student loan repayments are based on my adjusted gross income, and thus I can significantly lower my AGI through investing in a 403 (b), 457, or traditional IRA.

Then you probably don't want to do a conversion to your Roth until you have paid off your student loans, since it would increase your AGI.

One caveat is that I am not married, but this may change soon, and we would file our taxes married filing separately so that my student loan payments would not take her income into account.

Are you sure that filing separately will accomplish not counting your wife's income? This site on student loans talks about how your payments are calculated:

Income Contingent Repayment

(not available for parent PLUS loans)

This plan gives you the flexibility to meet your Direct Loan obligations without causing undue financial hardship. Each year, your monthly payments will be calculated on the basis of your adjusted gross income (AGI, plus your spouse's income if you're married), family size, and the total amount of your Direct Loans.

This wording seems to indicate that you add your spouses' income in addition to your AGI. And you would only have an AGI that was separate from your spouses' if you filed separately.

Seems to me that rather than trying to game the system, you'd be better off just living together until your loans are repaid, or else just bite the bullet and repay your student loans based on your joint income.

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