Having grown up in Florida, I was paranoid about the wind and a potential fire and sure enough at 10AM one broke out in the vacant lot adjacent to our property. 

With a backup plan, and proper (extensive) legal docs, much of the risk can be mitigated.

Purchase contract should show the entire legal as platted.

There's a lot of timing to consider, and honestly, this potential first cost segregation will be a learning experience for us. 

Ideally, I’d be buying and selling and potentially managing properties as a job, and be working the gardens and hobby farming, potentially attending farmers markets on weekends (we both love to create things).

Lend's the highest potential for such folly. 

This is not tax or legal advice, just what I personally do, consult your professionals! 

Do you have a step by step list when looking at the potential house?

A financial calculator and legal pad might work in the hands of someone who knows what they are doing, but that doesn't mean it's the best way to do it.

“Broker” is a legal term that often requires standardized coursework and a state license.