Then they won't need an upfront payment for work they haven't provided yet.Also, get a signed contract, copy of the drivers license, contractor's license and be added to their liability insurance.

Weather also makes insurance more expensive - wind and hail damage properties. 

Its also a good idea to build relationships with realtors, contractors, insurance agents, real estate attorneys, and property managers in your area so take advantage of events, conferences, and meetups.

Even in the nice locations, most top out around $2,800.Of course there is also your increased insurance, vacancy, repairs, CapEx, and the never mentioned reduced rent on the main house since having a stranger living in your backyard usually isn't appealing to most renters. 

I'm light on capital so paying a mentor isn't an option, but happy to split revenue (pay as I learn).I don't currently own in Florida, but from what I've read, the challenge is in even getting insurance.

For the person that is letting you arbitrage their property, why would they choose to let you arbitrage their property rather than hire a professional, licensed, insured PM that has a team to run their property for them? 

Licensing fees, CE classes, E&O insurance, general business liability insurance, sentrilock/suprakey fees, board association, etcc.

You need to carry a special type of health insurance, not the traditional kind.

Insurance is the FIRST line of defense.  

Title insurance, if paid by Buyer6.