@Joe Jensen, talk to lenders BEFORE you buy so you know the lay of the land and have your financing options lined up for when you are ready to move.Not every lender has a seasoning period of 6-12 months.

We’re still very busy late into season, and no sign of slowing down.

I know there are a tremendous number of factors such as seasonality, pickup, quality of the listing, etc. but I'm currently working on going through things to put pen to paper to write out why.All that said, Pricelabs (the tool I currently use) has recently added a feature to their dashboard.

When the first snowstorm hit while I was remodeling, I found out that the city does not plow all the side streets, only the main arteries.....So now we're open for business and I'm trying to develop a strategy for this coming snow season....I can't have guests showing up and not able to get to the property, and I cant require 4WD for all guests.

However, another attorney had mentioned having $10-$20MM dollars worth of coverage per property, which I thought was astronomical.I would appreciate any seasoned real estate owners or RE professionals to chime in. 

From what I have gathered you are stuck with a minimum of 6-12 months of seasoning if you would like the refi to be based on a new appraisal price and not the initial purchase price.So, my issue is if I fix a property in 3 months and its now rented out, what do I do?

Like I have seen in my country the youth are willing to spend their money on buying property than the older generation because they're more educated.

However, after reading and informing myself I understood that I’d have a better ROI by getting an apartment that needs renovation and do rehab.The problem is that older building here are really crap old.

Those not familiar with the market for a single family (semi detached or row house), your starting price is well over $500K for an older home (and that is outside of Toronto). 

Some having a seasoning requirement.