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I remember the excitement of "a world of opportunity," and how much it sucked as weeks turned into months and opportunities failed to materialize, failed to draw my attention, failed to come to any sort of fruition.

To my dismay today, my tenants just told me they are both moving out after all. They have made no complaints, been wonderful, but the main girl is moving in with her girlfriend (I would too - their location is much better than this one) and the other girl is moving out (why?) (why can't I keep women in my life for more than a year or two?) I've checked and I can still pull $1500-$1600 for the place if craigslist is any indicator. They want an out date of 9/1, perfect.

But...do I want to rent? What if...what if I gave in to the idea that I might work this job for a while, and just sold the old place? It's half a story above the ground, and there is no telling when some asshat upstairs might flood the place. Bugs can walk in any time. If you let it get too humid in the dead of February you can get mildew on the windows (condensation). It strikes me as a riskier venture than this place. So...what if I sold it?

I've been feeling poor. It's odd - I run a budget, and with all expenses and income accounted for I show a slow depreciation of my assets. However, the budget is rough with expenses over and income under estimated, so the reality is a slow profit. Still, my cushion could be yoinked by a car purchase, and by car I mean honda civic.

What if I sold the old place (currently a rental, near-ground floor),
moved to Beltsville / Rockville / Silver Spring (shut up BOTH of you), had a super speedy commute,
and rented out this place? (top floor, nice kitchen)
This place (top floor) shows 200% better, has no possible maintenance issues, and has a gigantinormous mortgage (2 actually) which becomes tax deductible if I then rent it out.

OH HOLY SHIT - IF I SELL THE OLD PLACE I GET A...WHAT IS IT, $250K TAX FREE GAIN BECAUSE I LIVED IN IT 2 OF THE LAST 5 YEARS!?! Sure I'm poor, but hundreds of thousands of dollars tax free? Would that make up for selling in not-the-best market? Best of all, to get 2 years it would make the most sense to just stay here until Feb 2009 at the minimum (so no need to worry about quick decisions of any kind). On the other hand, with the economy fuxored, the dollar weak, and new real estate set for a long downturn, where could I put money that it wouldn't pizzle away?

Help me out, oh diverse group of LJ people with various perspectives:
1. Think I should sell the old place (near-ground floor, currently a rental unit), or rent it out?
2. Think I should move closer to work, even though it's back in MD?
(note - the earliest I could move and take advantage of the tax-free profit, if there ever is a profit on the new place, would be in February 2009) (I'm not talking about selling the condo I live in now - I love it, it has no maintenance issues whatsoever, and is remodeled so nicely it would be cake to rent it out in the future should I move)

All input and perspectives appreciated.