If you do have an entity, treat is like your ex - stay as far away from it personally, do not mix funds and operate it at arms length. 

This will be the way to get them adjusted to assets that they will take over like I did from my dad.I look at multis and mixed-use to buy for my son to house hack, but NJ is crazy on pricing.

At one of our areas of mixed use, no residential is allowed on the first floor. 

What’s the neighborhood and unit mix?

You'll quickly see why AI is not the solution here... not only will it give you a random number from a site that posted it, but it will hallucinate and draw quirky assumptions into the mix like oh based on this % appreciation and applying it forward/backward, etc.

Strategies like furnished mid-term rentals, renting by rooms, mid-term/short term rentals or creative mixes of these can be considered too.

Start with a Clear GoalDecide what you want from real estate: Are you seeking passive income, appreciation, or a mix?

You and your friends have a great mix of skills and having a mentor is a huge advantage.

Are you looking specifically for insurance placement companies or corporate housing or a mix?

The first being - don't bring your friends or family into the mix :)Since it sounds like you're pretty solidified in your friend moving in, and it could be a good first roomie, so just to get your feet wet... i'll double down on Laura's advice - do a lease, for the legalities, but i also highly recommend some sort of written (we call it a) Room Mate Agreement.