You want a property that has the highest probability of maxing out on appreciation.Once done, you would want to explore the options below to maximize your rental income:- STR- MTR- Rent by RoomYou should go into this understanding YOU will live in the worst unit - in an illegal unit in the basement if you can!

On the contrary, uncertainty is the breeding ground for creating wealth.The core of the issue is whether you are willing to step out of the traditional investment framework and explore new business models and market opportunities.

Quote from @Drew Sygit:My apologies w/my earlier post (below), I was on my phone and not laptop so it wasn't tagging.I will if I may add some additional thoughts...1) The appraisals I've seen in these markets are no where near Zillow estimates. 

I’ve done a couple of fix-and-flip projects in the past using a hard money lender (HML), which has its pros and cons.I’m currently looking at a couple more properties and trying to decide if I should go with an HML again or explore other financing options.

As a fellow Chicagoan, I understand your reasoning for exploring opportunities outside of Illinois.

They just passed another conservation ordinance for rural, and if you want to even add an addition to your property within LG city limits you've got to cough up 10k for the general permit alone. 

My approach is conservative and focused on finding properties that meet specific criteria to ensure solid returns.If you’re interested in multifamily investing and would like to explore potential partnership opportunities, feel free to reach out!

@Stacey OlsonRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Do you have a region in mind to buy in or are you just exploring the idea?

My best understanding from talking to reps is they have one local employee (in addition to vendors like cleaners, landscapers...) per 10 listings/properties.