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

I'm super curious in adding a multi-family home to my portfolio.

Hey, @Eric Kajka Welcome to the BP Family, and congrats on your first "Live and Flip"!

Currently own my primary residence and 2 investment properties are a beach condo (short term) and single family home (long term rental).The problem is I run a successful business and have no time to do the research in new markets, deal flow, upgrades, making sure cashflow, property management, etc.I am also not a real estate professional.

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. 

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.

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. 

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

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