What started off as primarily a second home with the possibility of short term leasing quickly flipped to a STR first and a second home when not rented because demand is so strong right now for STR's in this area. 

I don’t have a specific recommendation off the top of my head, but for HOA/condo insurance, it’s usually best to start with a broker who specializes in multifamily or association policies.

In my personal experiences a lot of structural items start with bad drainage.

I just don't want to start working with a realtor and waste time and end up with no real solid prospects for buying.

--Searching properties:Size: 0-2 bedroomsPrice range: 300k maxI've started looking on clasificados, and trying to determine where to search.

I'd start talking to her and looking for another place for her to live. 

Personally, I started off getting referrals from other real estate investors when building my team but eventually found and added my own people to my network over time.

It will be a while before the negative equity starts to be recovered.  

The best time to invest is always in the past, but that isn't possible, so the only thing you can do is start today.

At least you have a starting point.