(My husband handles the funding portion)

At $250k your average 3 decker should put around $800-1200 a month in your pocket once everything's paid assuming you fix it up nice after you buy it and put in good tenants(which can be found in any area, it just takes a bit more screening to find them in the areas you described, you could hire a good property manager to handle this part).

The chances that you'll find a general contractor to handle a renovation cheaply enough to make you money on this deal straight out of the gate in January are LOW.3.

These dogs are immaculately trained and certified to handle nearly all situations and obey commands religiously.

Do you have someone outside of your business handling the draws, with inspections, etc.? 

They will handle pretty much everything and that should allow you to scale with no direct employees.

Nuisance things: paint, wallpaper (very annoying), holes in drywall, smells (unless it is a sign of mold), cracked windows, missing or damaged screens, no GCFI, flooring, broken handles, damaged cabinets, interior doors on exterior entrances (I see this a lot), bowls under sinks to catch leaks, general run-down-unlovedness.

Especially since, like you said, their E&O insurance does not cover me as a principal and if anything, God forbid, happens it will be my company's insurance handling the claim.

What issues arose and how did you or how should you’ve handled it?

Some people just can't handle investing or property management, same reasons.It's a question you have to answer for yourself.Add up your NOI and your paydown from what your tenants contribute.