(any wet spots, mold spots, bad drywall, etc is now hard to see because of the fresh paint, if there is any)I'll keep all of these in mind.

For number 2, you can have numerous ones and just apply later.

I'm thinking a partnership on the first house just to get my feet wet. 

Side note: A silicone roof is extremely slippery when wet so please keep the unit at least 15' (osha issue) away from the edge unless you have a 42" high a parapet on the roof.

I'm currently looking for the best way to "get my feet wet" and I thought buying a fix-and-flip home may be a good way to do that and use the profit as a downpayment toward my first rental property.

A friend has a 1910 home in Oshawa and has had numerous issues.

I'm not convinced it would be absolutely water proof like vinyl, but we ran it through entire house and caulked edges of wet rooms as added precaution.

I think that you should find an equity partner and get your feet wet with someone else helping move you along. 

Partnering up with other people is a great way to get your feet wet if you don't want to go at it alone.

As it turned out, the house had numerous defects and I told them we would have to renegotiate or the deal would be dead.