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

I live about 3.5hr away but have a full time job, kids, and other commitments that make DIY challenging. 

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

Connect with professionals in the real estate industry, including investors, lenders, contractors, property managers, and other experts, to establish relationships and access potential opportunities.Begin by investing in small properties such as single-family homes, duplexes, or small multi-family properties to gradually grow your portfolio.

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've buried more people in my family than I would have liked to and it's all due to poor health choices.