Buying TK is akin to gambling and something tells me you wouldn't take your hard earned money to vegas and play craps our roulette would you?

I don’t feel it’s growing as fast as other parts of Lexington, so it feels more like a gamble.

Her job has her gone from home a lot of times either off shore or just out of town and when she is gone she will ask me if I can stop by the unit to check up on it or grab her packages or adjust her thermostat so the a/c is running like crazy. 

However, if one could pick it up for say 10 cents on the dollar, could be a gamble willing to take.  

But isnt that more of a speculation/gamble as opposed to tangible money?

It's a little bit of a gamble, but if it's a relatively small volume then you have more possibilities.Is there anything stupid about this strategy?

One thing I'm not sure of is location in this case, I suppose I could either look in a well established area and expect equity to increase through remodeling or in a less desirable area that I'm gambling will attract more attention in the future.

The reduced tax on repatriating funds that have been sitting in offshore accounts for years.

Playing the appreciation game can be like gambling, and if your house is really cash flowing well after all of your expenses and your mortgage payment I'm not sure if it makes sense to sell. 

If its negative cash flowing NOW and you don't have a ton of reserves to cover yourself long term for the HOPE/GAMBLE of the appreciation play, then its time to sell, cut your losses and move on