The best thing you can do is to find an expert investment specialist agent / broker who can help you narrow down your search and help identify the best neighborhoods that you're looking to invest in to accomplish your goals. 

Can my property management company manage the property and receive the income?

I found this page through a simple google search of "how to leverage a paid off home".

Now, I've paid more than $40k over the years but not with one mentoring company.

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

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.

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.  

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

Do you buy IPO stocks or power companies?  

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