When I bought the place, he lived on the 2nd floor, the 3rd floor bedroom was his office (rest of the 3rd floor was empty) , and his cat lived on the 1st flor apartment.

There are a lot of crappy wholesalers out there and they make the rest of us look bad.

I pick out the great flips, and I am then supposed to wholesale the rest but I hate it so much I sabotage myself and end up doing nothing with the other leads.

Great if you are not afraid, just don't drag the rest of society with you.

You need to be better than the rest.

Do they just take back their $70K and leave the rest in equity or do they say "oh well this is no good.

I would anticipate 5-7+% gains for the next 5-7 years as Windsor plays catch-up to the rest of Ontario. 

But unlike pretty much the rest of the world, I didn't just jump in.

If so, I know a lot of people get second homes that they visit 5 or 6 times a year that they STR the rest of time so I know it is possible but I am not sure if this is allowed or not and I am assuming a lender would notice this when they see the insurance coverage on the property that covers STR?

If you have all of your properties under separate LLCs, then if someone files a lawsuit pertaining to one of your properties, then the rest of your properties will not be affected by the lawsuit.