If you're in a building that allows STR, the board can usually change that at any time. 

I want to buy condo units for less than market value by buying them from distressed owners and then renting it back to those same owners so they can continue living in their home and can avoid the challenge of finding something else to buy, or finding a comfortable place to rent.I'm in Ontario (Canada) and in my province Condo boards (HOAs) can unilaterally decide charge additional fees to fulfill the Condos obligations.

As you pointed out in point #2, this is probably a very emotional time for the seller and if he ends up feeling like 'you pulled one over on him' it could end up with a phone call to the Ethics committee of your real estate board. 

Vinyl siding looks cheap, so if you're selling to a clientele that is used to cement board siding, I think you will a rough time selling that house.

I am sure there will be folks on the board that will take serious issue with my approach.

I'm new just like most people reading from this discussion board.

Trex is a recycled plastic board that looks like wood.

If you are considering painting the cabinets, you should check out chalk paint.  

So I offered my father, what if I invested themoney to fix property and manage property so we could increase rental income and we would divide everything across the board including a sale of property once everything was said and done.

In a real estate transaction there is a uniform profit/commission for a real estate agent across the board that is recognized by the industry as a whole, this doesn't exist for contractors.