And there is the universal omnipresent market immune opportunities of; Distressed/ Exhausted/ Novice landlord, Death & Divorce. 

Have had two instances of the furnace in that same unit going out, both times cause a bird flew into the exhaust and lodged its head into the fan.- AC in my unit that we lived in went out twice while there in year 1, maybe year 2, spent about $800 to have it pressure tested (lesson learned here most home warranty companies are garbage and do not cover testing your HVAC so idk how you trouble shoot it without testing it, but the testing and refrigerant are not generally included) chased a leak for a month and ended up having them replace the line-set to the system for $1400.- AC in the other unit went out a year or two after that, was not a big issue, just needed one of those jump starter things, and some refrigerant, but was about a $800 fix to get it done on a weekend.- Roof vents were not secured correctly, so that lead to a leak into one unit when it shifted, was about $750 to get the vents secured and have additional ones added to bring it up to proper number.- Still need to get the gutters done, they need cleaned and one of them doesn't drain as it should.- Main water line and entire meter popped off the main supply line and had an unimpeded 1" water line dumping into the basement on mother's day, was about $1400 to fix, and basically an afternoon of waiting around for city and fire dept to turn on/off water at curb. 

To answer your questions as asked:1) Ask for an agent to do an analysis or pay for a BPO from a real estate broker (going to be cheaper than an appraisal) 2) Yes, multiple ways to get this done, we do cash outs before 6 months frequently. 

It honestly might be easier just to buy into an existing brokerage and be a part-owner rather than an originator. 

A renovated 100 year hold home could be in better shape than an original 1970s.With that said, you don't know what you don't know.

In an attempt to address this "fairly" we have 3 categories:Maintenance: small jobs our handymen can easily & quickly handle like faucet & drain leaks, caulking, snaking drains, tightening loose handrails, etc.Since the list can be exhaustive to define, we capped this category at $x, which is also tied to our owner approval threshold for efficiency. 

The only down side is that there needs to be an exhaust for the portable unit and typically this means one window cannot shut all the way closed and a piece of plastic or plywood be cut so that the remaining space is fitted with the exhaust flex pipe. 

We have exhausted all other options in the area, there are cheaper options that would need to be a while-occupied renovation but I won't have time to do any renovating as I will be in a very intense training period while we live there. 

Crawlspace & attic inspection (vapor barrier, vent screens, bathroom exhaust, leaks)14.

Going in and changing all the billing for each individual labor line in the back end gets exhausting.