I was leaning heavily towards AppFolio after all was said and done.

@Scott Trench that’s where I’m leaning.

Looks like leaning towards a trundle bed with a desk in this room might be the best option?

I would lean towards continuing to rent out the first house.

It is risky to use anyone blindly...and there are entire discussions on how to vet vendors and it usually starts with leaning on other investors in your market.  

im leaning more towards home base.

But in all transparency, I'm already leaning very heavily on just learning by myself via online, YouTube,  Bigger Pockets, books, and Carleton Sheets No Money Down course.Thx in advance for any input.

fix-it-all (joint compound with some additives) is not suitable for exterior at allYes it will wick in water as the paint deteriorates, and cause more rot, and keeping a good coat of paint on it won't be enough long-term in many/most climates.bondo (polyester auto body resin) is a cheap-ish "alternative", although harder to get detail work just right and not really all that suitable anyway (maybe ok with a good epoxy / primer, perhaps?).

Personally, I'd lean towards diversifying your investments across the different locations you're considering.

I'm leaning towards a cheaper “band aid” solution but the leak still needs to be repaired the right way to make sellable and have it covered in sellers disclosures.