There are very frequently exceptions (like my example) to commonly held "rules," like never investing in cash flow negative properties. 

New York City and it’s suburbs are prime REI location, similar to Bay Area.It is the center of east coast jobs, and economic engine.Also, it is where you live.investing OOS requires large capital, big investment and frequent trips.

I know you guys frequently see posts where the poster doesn't include all relevant details, but there is nothing in that regard with this situation.

I agree about being a trailblazer in this respect, although there are already successful STR plays here, which is why I'm already using my own money to invest here (the oceanfront condo is planned for STR) and after seeing the trends around me, am willing to pitch to others on it, I watch them fill up frequently with both domestic and foreign tourists as there is very little supply of quality rentals here.You have definitely made me more deeply question my position on some things but I also have got to where I'm at, at my age by trusting my gut and I do feel good about my stance and approach to what's happening on the ground around me, in front of my eyes.

However, the small, local to the property lenders, community banks and credit unions frequently offer a lot of lending products that I don’t see at the bigger banks.  

I have considered making a career out of real estate, but frequently feel overwhelmed with getting started.

Green board is highly efficient in bathrooms and kitchens where moisture is frequently in the air, but it is not the drywall that should be set behind tile in your shower surround or any other areas where it can come in direct contact with water."

With no one renting the common spaces I have access to the property frequently to meet with tenants, replace the AC filter, check to make sure we are not breaking HOA rules, make sure things aren't getting destroyed, and talk face to face with whoever is there to resolve any personal issues before they explode (see, more work!).

I've heard property taxes in Houston have been rising due to frequent town assessments. 

Just inspect your property more frequently to ensure the tenants are taking care of it and look for the best tenant you can when you are doing your background checks.