We have even first-responder equipment ready (carpet fans, dehumidifier, puddle sucker pump etc) to deal with the issue quickly and curb the damage, before we get the contractors in to do the repairs.

I am pretty handy and have done plenty of restoration work myself and not afraid to put in some elbow grease. looking into real estate to get the wealth ball rolling but feel a little uneasy given the current state of the economy. what would you do in my shoes?! 

I would compare my return with any market, anywhere but 1) this is a different San Diego market than the one I have been so successful in 2) while I am a big fan of leverage, I am not a fan of over leverage.

Big fan of Portugal, and interested in investing there. 

If there was no appreciation, there is no need to do a 1031 exchange.I have never been a fan of condo's as you lose some control over the investment - You have no control over the monthly maintenance fees, you may not have control over who is on the board, you have no control over special assessments.I wish the investments turn out well for you!

Hotels are definitely not fans of STRs but it is regular people and safety officials that are pushing for these regulations. 

I'm sure someone on here has been in my shoes, right? 

WongNot everyone is a Quickbooks fan.   

I appreciate the suggestion to check out Tim Delaney’s posts - I'll definitely do that.FYI - I’m also a regular listener and fan of your BiggerPockets Money podcast, so it’s great to connect with the community here.

Or I've seen a few of them pay cash or do 50% down payments, which of course they will "cash flow" (I'm not a fan or doing over 20% to 25% down).