The only thing that's going to raise a flag to a lender is when the insurance policy comes back with a different owner and/or the tax bill comes back with a new owner.

I think there is lots of opportunity there especially given the critical mass of ~3M+ people as well as its position as a US flagged hub for the entire Caribbean.I have heard the same points echoed by  @Kathryn Morea   I have personally worked on commercial transactions in San Juan and Fajardo and also found there is a lack of transparency in the marketplace.

Any renter who seems in a hurry to leave their present abode is a big red flag. 

Avoid abnormalitiesAbnormalities can be a red flag for the IRS.

The house is going as is and the inspection report will show a decent amount of yellow flags that could potentially scare buyers.

And from experience, now no longer consider the property if it is: on a corner lot, on a flag lot, adjacent to a run down singlewide, has little back yard, power lines in the back yard, too far from town.We have been living in each flip as we remodel. 

All keep getting flagged and deleted.

I assume I'll be trying to get traffic from either Six Flags Great America traffic or Navy Graduation families.My main reason for purchasing in this area is to have a vacation home for myself.

They could find stuff on most any building across the city but once you raise the red flag they'll come at you from any advantage to again fill their revenue stream and of course protect public interest. 

Red flags for sure now 😫😆