That is a gamble.

I normally call references and run background checks on the first applicants to give me applications and fees, and move on to the next if the first one doesn't qualify.  

You really should be counting your holding costs as if you are using all other peoples money at the normal rate you would get. 

I would totally "house hack" or buy a duplex or triplex (which all falls under a normal FHA loan).

My second thought is that you might want to eliminate hotels from your future plans, a hotel is not a normal RE investment, it is more of a business, and that requires a lot more of your time and energy, plus there is a differant skill set involved.

*****Did your probate client inherit a distressed property that doesn’t look very nice, needs repairs and that won’t sell quickly using the NORMAL real estate broker methods?

Other than that it is pretty much a normal transaction to you as seller. 

@Justin HerringtonWhile Thorold does not give a maximum occupancy per dwelling unit in a direct manner, it appears to define any building providing lodging to more than four (4) occupants as a boarding house:“boarding house” means a building in which lodging is provided for more than four (4) persons in return for remuneration or for the provision of services or for both and in which the lodging rooms do not have both bathrooms and kitchen facilities for the exclusive use of the individual occupant;In turn, they restrict a rooming house or lodging house (but never marry definitions to that of the boarding house) as follows:Where a dwelling unit contains rooms intended to be used in conjunction with a rooming house or lodging house, the occupants may share a single bathroom provided that: (1) not more than nine (9) persons occupy the dwelling unit; (2) for each additional nine (9) persons or part thereof, there shall be an additional toilet, handwash basin, bathtub or shower; and (3) access to the bathroom can be gained without passing through: (a) a habitable room of another dwelling unit; or (b) an open area, which is not normally heated during the period of the year which heat is required by article 2.22.3 of this by-law.So, it appears to come down to whether boarding houses are permitted where you property is located (and whether they need to be specifically licensed), unless your building would be seen as a non-conforming duplex.This is the question, I believe Thomas was asking.

that is the crux of the matter... when jobs leave people leave with them and like we have out here in the West.. ( Ghost Towns)  its just normal commerce at play.

In a normal retail transaction this is usually after the inspection period is over and everything is good.