However, I’d imagine there are a lot of pain points and frustrations that come along at many points in the process that make you pull your hair out.

Many of the underwriters started providing the coverage in Florida until the DOI pushed back saying they were providing unauthorized affirmative coverage.

I am looking to connect with someone, that either can affirm my thoughts and underwriting or poke holes in it, that has experience in deals of this size. 

When I had a PM I stayed out of their hair completely.

Extra toiletries, GOOD quality hair and body products, offering to order them a shuttle to and from the airport, etc.

Assuming the photos accurately portray the overall condition of the unit and not just one bad spot that was missed, that's pretty grimy and personally I'd be miffed if I moved into a place with that much dirt and hair on the floors.

HOWEVER, upon replacing the air filter maybe 2 weeks ago, I see there's A TON of dog hair on the old filter. 

Today it is a mask and tomorrow it is a hair color or something equally unreasonable.

I know it sounds like I'm splitting hairs but some banks write HELOCs in their residential department....which won't write Investment Properties.

It's like splitting hairs, they are all very similar.That said, what you buy in said market is where you will see your biggest swings in ownership experience.