Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

My wife is a realtor and my sons are MLO's and we started a lending company last year :)We do STR's mostly personally with our own properties and self manage all of them.

I personally like the buy-and-hold strategy and we help clients who share this long-term, wealth building mindset. 

I financed the acquisition of the land with personal and private money.

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

I personally would recommend the last method.

I typically don't comment on other's businesses unless I know from personal experience.

Whether the seller was open to a buyer commission or not, I wouldn't put an additional cost into any personal purchase.  

I do know that unless a person knows what they’re looking for and how to close, it can take a lot of leads to get a deal to the finish line. 

A contract is only as good as the person enforcing it.