Basically, this made me realize that I need to define my goals a bit more clearly...anybody else felt like a failure after making 5k? 

All I know is that in my experience roof stock touches base on everything you have said you do not want to do, for example “play landlord” you basically just sit back and watch the money roll in (given it is a good investment).  

If this single family house were my only investment I would have struggled to cover the basic PITI, yes @Grant Cardone, you are right......  

Utilities (STR don't pay for those), replacement of basic items such as towels, paying your cleaners, etc.Are you buying here in SoCal?

Not my cup of tea, but Boston has a lot of great things going for it that in the long run I think you could make it work.If by multi-family though you mean a 5+ building that you're presumably going to look for in the Midwest or South...it's in its own bubble as a disturbingly large number of people who made bank in the last 10 years of the up market are shifting their focus to a larger scale asset and are purchasing these distressed properties which is driving cap rates down because people need a place just to park their cash. 

We have a unit downtown I birmingham that needs a basic rehab.

The property meets our basic needs, in a so-so area.

Have a friend who lives near your old home drive over and see if it is vacant.

Coupled with rapid population growth, it’s driving an affordability crisis that leaves many residents looking for homes far from job centers and essential services."

It goes against basic principles.That being said, if it were just a stop-gap measure, and not a permanent solution, I would just have to look the other way.