Should I stay or should I go?

[Kevin Reid]

This is less an investment for profit, and more about our home life I guess.

Our situation is we bought our home in Florida at the worst time! It was around June of 2007 right before the collapse. We paid 207k to build it, and at one point it was only worth 130k. While it has rebounded a bit, it's still only worth about 195k, and we still owe 173k on it after refinancing a few years back. So realistically we have 20k in equity, and can only rent it for about $100 more then the mortgage payment.

Here's the deal, the house is now 10 years old and needs some small upgrades (counter tops, paint,...). On top of that we would like a pool since we have 2 kids. So we all know a pool is generally regarded as a bad investment, and I might get back 25-50% of it's purchase price, but this is Florida and it's damn hot here, lol.

So we have been looking and not finding a ton in our comfort range. The homes we are finding that meet all our wants are generally in the 250k and up range, and will still need some work/gutting. Some do have a larger piece of land that I could build a workshop that I've always wanted, but it's something I can live without if need be. 

So what do I do? Should we move and possible add up to 100k onto our mortgage for a slightly bigger house and more land, or should I drop a 40k pool into our current home and try and be happy with what we have? Is the situation you know better then the one you dont? I don't know if this is really a factor, but I plan to retire in about 20 years, and besides the house we are debt free.

[Jason Hirko]

@Kevin Reid one thing to keep in mind if you move, your $20k in equity will get eaten up by realtor commissions and closing costs when you sell your current place. Seems like appreciation would be the same if you move or stay, so I think the best move financially is to stay put. Of course when it comes to your personal residence, I wouldn't necessarily suggest you always choose the best investment.