Hi Eric - I agree with so many of your points. There is actually a pretty active investor community here on the island. Also there are many posts on BP. I have alerts set up and so I see some of the chatter. However, I've had to work with BP several times as the territories were not listed as a way to search or post. For example, we have meetings every month and sometimes I'm forced to post the location as Florida, because San Juan doesn't show in my list of options.
Btw, the bankruptcy is now over, as of about a month ago. FEMA & CARES act money to the tune of billions are flowing in to the island as we speak. There is incredible investment into the infrastructure, the likes of which have never been seen.
Financing is a bit more challenging, certain loan products are nearly impossible (hard money loans, construction loans) and there is no central MLS that is used (there are 2 MLS services, but not fully used) so comps are difficult. These are not insurmountable, but they are barriers to entry for some folks. For cash buyers, it's a dream.