My heart would like to let him stay for free but I doubt I can afford it and also, I’d like to make sure my interests and his are adequately protected in case this get “squirrelly” in any way.

I'd tell them if they want you to pay $8K in closing costs, then they need to up their offer to $224K to cover the extra $4K in closing costs.What does your realtor suggest?

I don’t think I’d be excited about your height on an ocean front Caribbean island.

I'd like to hear more about the Uber scene down there.

Unless you have boots on the ground near there, I’d focus on cities a bit closer to Indy.

Which in turn will bring plenty of other investors and general business to the area.

I’d love to connect with you further on these deals! 

Hi Layton,A friend sent this post over to me so thought I'd chime in.

I have used them plenty of times for my personal LLCs. 

Again, it looks like you have already started to do most of this which is great.If you have the flexibility and given you've already indicated a desire for a SFR or Small Multi...I'd buy a small multifamily and live in one side and rent the others.