You have two homes so you already have rental potential to cut you teeth and getting two or three more single family homes as part of your rental portfolio would not be a large outlay.

I'd rather cut teeth on a small property and be out $15-20k vs trying to invest here in, say,  SoCal and potentially lose hundreds of thousands.

Magic erasers will abrade paint finish, so it works fine on flat paint, but be careful with enamel through high gloss finishes as you may make dull spots.

If you have already cut your teeth on other rental projects, I'd quadruple check all your requirements. 

I do enameled steel replacements, but that has its own series of headaches and a learning curve that you have to get used to.

Plus it sounds like you’d love to own rentals in the future, why it cut your teeth and get some experience by buying a 3/4 plex?

The house being there is just gravy on top and seems to be a great opportunity to cut my teeth and grow as an investor.

If that's right, seems to me the FH laws don't have a lot of teeth. 

Lending attorneys can be as rare as hens teeth and I bet you hear the same few names, so call each one.

Make sure you use the right paint (enamel).If the trees are rubbing on the roof, then trim those branches back as they will damage the roof.Sprinkler heads can easily be replaced by yourself if they aren't working.Garage doors, replacing the kitchen, timer for the sprinkler...to me I'd leave those.