We feel your pain here in the Short-Term/Vacation rental forum.

I've sold a house to a FHA buyer and it was a pain. 

@Chelsea Ray Soooo sorry for your pain Chicago brother.   

Payroll withholding is a pain in the ***, straight up... both in calculating it and paying it.

Similarly for "unused" chimneys - are they snow capped or bare (heat escaping the building);Windows - broken thermal pains are obvious;Heating Plant (boiler/furnace) - is it running correctly or are there issues (gurgling or short cycling);Tenants - are the windows and/or storms open (with the thermostat cranked) - we reduced the previous owner's heating bill by compelling  enticing the tenants to keep the windows closed during the heating season.The key is to profile the "unloved" properties when they go on the market in spring or summer and then buy them in the dead of winter.

It seems there are a lot of issues down the road with transferring properties into LLCs due to “due on sale” financing clauses and transfer taxes (2-4% in PA), in addition to the legal ramifications.

I ended up investing in Indianapolis IN because it's better cash flow.The only reason I'm commenting on your post is that I want to clarify that A class neighborhoods generally attract A class tenant but A class tenants are pain in the butt!!

Some growing pains and I didn't like being on-call/on-internet 24/7 for things that pop up while scaling.

I kind of just followed his guidance but what a pain in the rear. 

Here are some of my pain points:Given a particular property, what would be the typical expenses for this building?