I paid a licensed and insured company, who is pretty big in our area, to replace it. 

A great PMC (Property Management Company).Whatever rental you buy, they have to deal with it every day. 

Similar to if you hired a company to replace a roof-you don't have a copy of the bill for all of the shingles and nails, but you have a copy of their bill that has those effectively built in.

The agent told me that Tower Hill (the insurance company) can’t adjust the occupancy status and that I’d have to rewrite a new policy for occupancy.

Every area will have its own distinction....like NY/Boston/Chicago etc there may be A properties that are 100+ years old and there may also be brand new to market assets.

Talk to an (investor savvy) agent or STR management company while you are there. 

My company has done 1031s for 31 years, we work in all 50 states, and we're very good at what we do. 

I have started a property management LLC company to manage these properties for myself and hope to grow that business as well. 

Hi, I'm in the process of starting a vacation rental management company (already have clients ready to signup) and would love feedback from other property managers on best management software to use.  

(I'd just add to his video the idea of having a plumbing company set up so that your tenants can call that company directly if they have a plumbing emergency.)Don't compare yourself to your friends.