@Mike Dymski, Totally agree that a professional investor is an investor in all weather whether they're buying umbrellas or sun screen. 

It's the nature of the business.I wouldn't recommend hiring an agent since most agents aren't familiar or comfortable with the areas you would be investing.Your best bet is to find professionals in all facets of the process in the market you choose then fly in to town for a couple of days.

I've talked to 3 mortgage professionals, and they have all told me no HELOC is possible because I now have something considered to be a multifamily property with a primary loan on a single family property.My goal is to take out a $25k loan to pay my mortgage down and get out of paying PMI. 

It may be time to look at senior housing of some sort. 

Student housing, parolee housing, senior living facilities, drug rehab related, military housing.......

Certain buildings will tend to appeal to other types of tenants; professionals would be interested in different things that retail businesses, etc.What amenities are important to you? 

Sure you may get some business from it but operating off of fear and not allowing other professionals to come doesn't make it look like you are coming from a place of giving. 

Unless you insulate EVERYTHING and put in good electrical heaters and have a professional do the work then think twice about it.

Up to six months of HOA dues will be senior to the first mortgage.  

I am currently an IT professional and have been for roughly 8 years after leaving the USCG (Avionics Electrical Technician).