'Pooling' would be something that requires compliance with the state and Federal regulations for USA based investors.

It takes most people months before they find a deal and feel comfortable pulling the trigger.

You should probably reconsider having him serve in that capacity based on his clear lack of good judgment, or at the very least make him read the landlord-tenant handbook front to back, especially the part about a tenant's right to privacy and the part that states: "any uninvited sexual advance, solicitation, request, or demand for sexual compliance is considered harassment" (at least that's what it says in the handbook for my county and I'm sure something similar appears in most if not all).

I would understand what homes sell for, what they rent for, and how much cash you will need to build up in order to pull the trigger when you are ready.

Can’t someone just “gift” someone a certain amount of money per year anyways without triggering taxes/etc?

The best thing to do is run a benefit estimate before deciding whether you want to pull the trigger on cost segregation.

I have been interested in flipping house and buy and hold RE for a long time but did not pull the trigger until I bought a live in flip in 2015 and have been working on it as I acquire the funds since.

Real estate requires thick skin and its so obvious how easily you are triggered.

This is my first time actually pulling the trigger and going after this .

Someone who will review my documents and records, help me determine the best options, and pull the trigger.