Im wondering if I'd have better luck making more money off of multi family elsewhere.can anyone tell me what markets they'd recommend for house hacking/ multi family and if Chicago is still a good choice? 

Your best option for this to happen are in a couple of zip codes but specific areas of the zip codes.Your issue is going to be property value so you need to be very mindful in your choices.

I view the same as vacation homes, yes they may provide rental income when not there, but you will use them and they will most likely not cash flow so not great for investment purposes but lifestyle choice.

One likes a larger number of units and doing syndications, while the other likes lower number of units and partnerships.

Buildium seems to be a solid choice that a lot of investors trust.

@Tair BitonWelcome to Milwaukee investing — great choice!

From what I’ve seen talking with operators in my Co-Investing Club, focusing on design choices that add perceived value without dramatically increasing costs tends to make a big difference.

That zip code is a good choice because of the airport.

I am an Executive in a life sciences company which takes the majority of my time and I have no intention of stopping that, but want to build a larger rental portfolio to have other financial / lifestyle options in 10 years. 

Over time, I shifted toward passive investing, partnering through my co-investing club on larger projects where I don’t have to handle day-to-day operations.