My old boss had a saying, "throw yourself into the sh*t, and see how you smell when you come out."

That would be throwing good money after bad. 

Not to throw a twist in all the comments but I would put the property in a Trust.

The building would stop throwing off cash, and I'd have a big pile of cash, but no longer the excess monthly income I think needed to help qualify for a new loan.3) Do I sell and try to 1031, but it would have to be a big building ($4mil +) now with double the property taxes, a new loan, and I'm not sure I can find something that size?

This is even more of a no-brainer if you're throwing away money every month on rent.One thing to keep in mind when looking for an FHA owner-occupied triplex or fourplex is that 85% of the market rents on all the units need to cover your monthly payment (principal, interest, taxes, insurance, and mortgage insurance).

Often times, a contractor will throw out whatever number they think they can get away with having you pay, but once you break it down to labor and materials you figure out that their bid is the equivalent of them making $200/hr or something crazy like that.Keep meticulous records of what jobs actually cost, labor (both hours and dollars) and materials.

What should I throw money at?

The market here in Edmonton, Alberta, Canada (look at me throw out those key words!) 

Throw in a home office and you've got some pretty fun math to do spread out over 3 or possibly 4 different schedules that has to be done exactly correctly and, (trust me on this - I used to work for TurboTax), most self-service tax software programs are simply not equipped to handle this easily and you must answer the interview questions exactly perfectly in order to get this right.

That means you need to put your marketing (in this case your for rent post) in front of the greatest number of your target audience (potential renters).