This isn't my situation, but one of a family member who has asked me what I think.House is owned by family member, let's call this the RentingFamilyMember.

What did you do with all of that space/how did you divide it, if at all - multi family, short term rental, other?  

Melanie,I don't have a STR arbitrage, but I do own a single family STR. 

Investment Info:Single-family residence buy & hold investment.

Chicago Lawn is a much different area than Woodlawn or south shore - there are a lot more single family and small 2-4 unit properties, and the area is less dense generally. 

If one were looking at house hacking a multi family property, at what point should you set up the entities (LLC and a trust) ?

Investment Info:Small multi-family (2-4 units) buy & hold investment in Oceanville.

I've rented two homes over the last few years, and I'm interested in slowly buying more single-family homes and keeping them long-term.

I need some advice, I continue to learn everyday, listen to podcasts, read ect but I still find myself unsure of what to do next.Basically im 22 I have 3 properties I own that are STR and all BRRRR'S besides one that is free and clear due to it being old family land that was vacant but had basically a 500 squarefoot teardown on it. 

Hey, my wife and I own a variety of properties… warehouses, single family homes, self storage, commercial buildings, multifamily etc.My son is turning 18 in December.