Doing a project house myself right now, wrapping up.

Then half of those don't probably don't make sense ROI wise for most people, and maybe 1/2 of what's left you can rule out due to location or some other factor.#4 While I am sure there are plenty of people that do it, the worst situations I see are investing with friends. 

Am I thinking about this the right way?

We BRRRR 8-10 per year and the flips supplement the money left in the BRRRRs. 

I've never tackled a deal quite like this before, and wanted an outside opinion to see if I am on the right track or completely overcomplicating this deal. 

Before he closed on the property I pointed out that his property taxes will significantly increase after a year when the property appraiser registers the new sale, and that insurance in Florida is going up by 20-30% a year right now.  

So, lots of people to connect you with to find the right fit.If you have any other specific questions, I'm here to help just like everyone else in the BP forums. 

My brother is a GC down there who does some great work so it would be right in our wheel house.

You're essentially loaning someone $100, 000's of dollars at no interest for an undetermined period of time with no guarantee of getting it back, right?

House hacking where you get to "live for free" is near impossible with interest rates right now.