In tenant friendly jurisdictions like Chicago, they target mom/pop owners who don't know the laws to statutorily screw them - The landlord can either pay the tenant $1k to settle and give them 60 days to move out along with a good reference, or they can pay $3k + $8k legal fees for a simple error.

If you're itching to start out, I might suggest starting with something more passive to get your the portfolio started, while you learn the ropes for something more DIY / hands-on (just assuming that's what you want, given your reference to management skill).

Would very much appreciate any direction or references to an agent specializing in multi-family or an owner looking to sell their property in the area.Thanks!

It is not a solution to the problem.

Bottom line is I don't often start new threads to ask these questions...therefore the number of posts I make goes down.Furthermore, when it comes to answering questions...I like providing people with references and resources more times than not rather than just my opinion.

not sure what you mean, Hillary Clinton reference?

I would not thought of this siimple solution.

@Mike SavageZillow is just for reference .

(flipping, rental, mobile homes etc.)I think finding the partner with experience  would be the perfect solution in my case.

It may be worth looking at dedicated maintenance solutions like Latchel for emergencies.