He was an absolutely amazing agent and I would highly recommend his services.

It's highly likely the people that came out were simple tree cutting services, not educated arborists (who gets 3 estimates in an emergency?)

Engaged a real estate agent and visited five properties, with plans to submit an offer on one today5.

Understand that a caretaker is a service that you will pay for. 

Unless, your offer is much lower than the asking price.

Our offers are cash, no showings/open houses, and buying as is.

I negotiated it by putting in an escalation clause in my offer since there were 8 other offers for the property.

@Brett Dudley the inspector for any buyer should catch the roof needs replacing and any other major issues, which should lead to the buyer renegotiating/lowering their offer price to cover these.

The regional ones tend to have most or all of the same services but tend to provide much better customer service. 

For $1-2k per month operators can generally hire a dedicated local 'Superhost' or experienced local manager/cleaner while enhancing the quality of services rendered.