This stuff doesn't have to be complicated.

I have a mix of MTRs, STRs, and a room rental and I can perform all the needed property management and bookkeeping features on the site. 

Stephen, When I open the link to the Cape Coral site, its just to the Citizens shared services page. 

This will allow you separate business income and expenses from personal income and expenses.Since you plan to house hack your bookkeeping and tax return preparation will be more complicated because a percentage of your home expenses will be personal deductions and some will be business deductions.

There have been a ton of warning signs here on BP and other sites about the markets and how to be a smarter investor - but that is boring advice.

Clearing potential building sites.  

Things they did bad which I wish I had asked more information about:Never involved in the screening of tenantsThey recommended keys for cash by waiving the rent amount buy only collecting fees which they would get not meThe cost to evict is 750-950 yet other companies told me they will include eviction in the priceThe tenant didnt pay in full last month and I was the one calling out to them and asking questions then a few days later I get an email saying something happened with the tenant and they are investigating.You get passed from person to person every week or so.No one told me when the construction was complete and so the house was ready for a week and the post to zillow and other sites was not done.It took them another week to take pictures and then another week to upload it.I was paying 200 dollar a month electric bills while the house was vacant because they left the AC running in the empty property.

City-Data and Census.gov are solid resources, and sites like Rentometer can give you a good sense of rental prices.After that, I narrow it down to neighborhoods with strong fundamentals—good schools, low crime, and convenient amenities.

I think you may be over complicating it.  

Costs a lot less to do all pad sites together versus individually. 2.