Talk with your insurance agent to make sure you have the correct policy(s) in place if/when you decide to rent it out to another individual.

If you want to help your brother teach him the same money / rental strategies that made you successful.

I ask because some other lenders that I had questioned advised me that they would only lend in individual names.

I'd like to build a community around me of like minded individuals. 

Some teach...I think "retire" is a term that needs explored.

I would call that middle class at least, and that's assuming 0% interest on that initial $3.5M.So, you're ***-u-me-ing perfect health, no injuries / accidents, no natural catastrophes (hurricanes / cyclones, wild fires, volcanic eruptions, ... at least two of which are common in HI), vehicles which last forever and never need to be replaced, destruction-proof housing and furnishings, ...... and if you CAN live that lifestyle in HI on $100K / yr (most people can't in ANY state), why are you not teaching personal finance at the university level? 

I would ask about individual private lenders and how to find out if they're legit or pranks

If you are wholesaling to 3 different individuals it may be easier to do 3 different contracts so you can close all of them at different times.  

She not only teaches wholesaling, but she also does it daily...Let me know if you have any questions or comments, happy to help!

It will teach you just about everything you need to know about getting started in investing.