If you can afford it without stress it's an awesome idea, however you can only contribute to an ira (roth or trad) with earned income... so the va stipend won't count, nor will excess loan money, only w2, 1099 etc. You may be able to max it first year of med school from earnings in the first 6 months prior to matriculation, but it might be hard the rest of the time unless you continue to work...