He went over there with his roommate on his own and dug a hole deep under the slab foundation to repair the leak all on his own.

Whoever is giving you legal advice is only helping you dig a hole for yourself.

*repairing holes in drywall and painting (not from nails but larger ones) *Removing blinds the tenant broke and replacing with new ones*Heavy cleaning where they did no cleaning at move out and didn’t apparently clean at all while they lived there I also understand that I need to provide an itemized list of repairs/costs and have 30 days to return it.  

Why would I send him down a rabbit hole that has no exit and then we are back to square one.There are variables on every deal. 

All it takes is a furnace replacement or a water heater replacement and your in the hole.

However I’ve always hated the idea of HOAs and feeling like I’m essentially renting my property, so I started digging into all the HOA docs (as of course any investor should), and fell down the rabbit hole of the HOA website.

There are ways to mitigate that risk with good management practices, but the best screened residents in these areas still run into life problems.Conversely, a .5% ratio house may not look sexy on paper but it will be nice and steady, appreciating in value as expected with outstanding residents that pay on time, clean when they leave and won't punch holes in your doors. 

What I mean by this is if you were to punch a hole into the wall you would be hitting the exterior wood siding.

Most of them don’t know their a$$ from a hole in the ground about investing or rentals ( now to be fair not all of them or the ones on here!) 

As the house was built in 1955 according to the sun there is lead paint and asbestos in the Attic and as I was to witness myself there is no real closing of the attic it's just an open hole in the side of the house where there is Storage stuff inside that hole.