IIRC you should get a Roth if you anticipate your tax rate on income when you retire will be higher than it would be currently. The deal is that you pay taxes on money you contribute to a Roth IRA (it counts as present income), but you don't pay taxes on it when it comes out. It's the opposite for as normal IRA. There are other things you could consider, like what changes you expect will happen to the tax code in your lifetime, but if you assume constant tax code then the question is basically how much income (money-deductions) you're making now vs. in pension when you retire.
idk anything about healthcare plans.