I find it hard myself when buying property not having an inspection, in fact, I like to get a regular inspection and a sewer scope in addition with every property I put under contract.

Find someone who is an investor, wholesaler or a real estate agent that would be willing to walk you through some deals and buy them lunch or coffee on a regular basis. 

Replacement Cost:  policy normally pay up to the limit (even if the host costs more to rebuild than the limit)2.

Read some studies (but consider who paid for them and their motivation :-) And cities like LA, Seattle, NY cannot blame the vacation rental market for their housing problems, those are the result of failed policies by years of leadership....Vacation rentals have many benefits over standard rentals that you might consider a) they open up areas to vacationers that would ordinarily not be accessible (not everyone wants to stay in a hotel district).b) they almost always improve the neighborhood they are located in - the house, inside and out, must always be in near-perfect condition in order for the landlord/host to stay in business.

Also, what does the umbrella insurance do versus the regular insurance policies?

Or do you just bite the bullet and get regular expensive coverage? 

Also, I use a software called Hostfully that helps automate processes and put together digital guidebooks.

And I really need to start seeing this business dole out regular and predictable profits instead of holding them forever. 

We travel regularly to visit the properties but I believe that is very important in maintaining a strong asset. 

There was a group that occasionally met in Gainesville that was hosted by a Realtor there.