I'm working on our married filing jointly taxes, for our first year. Our situation last year was similar (although I did get to deduct part of our moving expenses since we moved for my job), and we only rented out our old homes for part of the year. Nevertheless, we went from getting thousands back to having to pay a few grand. I estimate the "marriage penalty" for us to be about $5000. If I get super curious, I'll do our taxes as if we were both single (which is how we are treated by our state) and see how that works out.
Learning excel for work has made me into a monster - I can now view the results on our tax situation if I raise the rent on my rent house, and can estimate the tax impact if we were to hold the properties past the point we can sell without capital gains. Anyway, for me, doing those kinds of calculations and projections is fun. Yes, really.
The question we must both answer is whether the modest income on the rental properties, which are rented to friends who probably don't want to move, is worth the gains we'd pay on eventual sale, particularly when we must depreciate our cost basis for the years we've rented out the properties. (another factor I need to build into the equation). We don't get to depreciate now.
We were thinking about an investment opportunity that looked attractive until I read the contracts. What I told C in explaining my decision was that we should use that money to help C fulfill her own dream, not fund the dream of a stranger. C agreed, when I put it that way. We are not gamblers - it ended up having too much risk for us. Anyway.
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