carrying 2 mortgages

Thought you sold the company and was rich as fuck.

Buy Dream home.
Rent out first home.

I never would. I'm timid that way.

Can't you rent the current house?

Possible, but its worth the try. Two mortages/rents sucks!

As long as you are realistic about the value of the house you're selling and not wasting 6 or 9 months taking cut after cut on the price while still paying the mortgages, you should be fine. Wasting months to get to the same point but having also paid 6 months of mortgage in the mean time is the wrong approach.

depends on the house you're selling. I'm in that boat at the moment and am not happy.

That said, I had good renters for the past two years, so the house isn't a shambles - but I still spent the better part of a day replacing light bulbs, tightening doorknobs, and other minor crap.

Most renters will screw you, that's why they are renters in the first place.

But it can be fun. Get insurance for the property, charge them a bundle in a security deposit, and that way even if they do destroy it you'll be covered.

A small part of my business is evictions for a couple of landlords here in the area. It's always good fun evicting some poor single mother from the pseudo-trailer park. About a year ago I had to file papers to evict a single mother with two mentally handicapped children. I drank heavily that night to soothe my conscience, I assure you.

Aren't you moving like ten feet?

Renting only delays the carrying of 2 mortgages. Very hard to sell with people living in there. Renting is also a headache, worrying about the property and the tenants and the like. Why give yourself that extra headache? I think renting is only something you do if you can't sell.

East Egg or West Egg?