I am just trying to switch practices from processing apps in the order they are received to setting a time period (say 24-48 hours) in which to receive apps & fees, then choosing which one to process based on the info provided and how I feel about them- I am getting pretty good at picking out the ones that will be a pain.  

Any downtown deals are immediately killed by assessments (even if you're looking just to buy for yourself) - because it becomes way cheaper to rent for a 3-5 year period... and don't even mention special assessments. 

The 24 months of residence can fall anywhere within the 5-year period.

If this period goes smoothly, then you will prepare to close.

The 45 calendar day ID period runs very fast. 

@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.

There would also need to be an agreed time period for the investment (for example 5-10 years).

I dont consider these areas to be a real problem because I am likely to have to deal with a lot of problems in a 4 decade period and flood can be one of themTo your successJosh

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

If your inspector is not familiar or unwilling to help w future code issues I would suggest contacting the village during your inspection period.