Thanks for the comments everyone! I think sdrealtor and others have convinced me that selling (at least right away) is a bad idea. As I self analyze myself, I’m definitely getting sick of corporate engineering*, but I’m convinced that’s a separate issue from whether to remain in San Diego or sell the house. I didn’t mention it initially, but my wife’s parents are getting old, so that’s another motivation to spend at least a year in St. Thomas.
ScaredyClassic’s description of a carefree life as a busboy smoking pot by the dumpsters certainly does have it’s allure… Not sure I need marriage counseling when I have your free advice though. Seriously, I my wife and I are closer in our assessment of our kids that I let on. She could be convinced to use our daughter as the property manager, and I could be easily convinced not to use her. Another factor is that she’s suppose to be studying hard, so dealing with tenants and broken dishwashers might not be the wisest choice.
Finally, if anyone else has recommendations for property managers, please send them my way. Again, I’m biased, but I think it’s a high end house (large, large amount of land, pool, ocean view, etc.) and should be marketed as such or at least the property manager should have experience with that type of house. Nobody chimed in with long term rental vs. short term.
Thanks all!
*I think I am just tired of corporate engineering, but another thing I’ve noticed which I wonder is just unique to me is this: either I’m getting dumber, or the folks coming out of university are getting much smarter. Not to brag, but I always thought of myself as not top talent, but definitely in the top 25%. Now I feel like bottom 50% or bottom 25%. Rather than a negative, I suppose the positive way to to look at it is this: the country is in good hands and things will only get better.