Stepping up to multi-family, Chicago area

Hi All,

I'm a reasonably experienced SFR investor, having bought, renovated, and managed a dozen units in Atlanta for some years (started late 2007). Much of this was me personally, until having a family and then in early 2017, moving away. Since then I've hired a management company and fortunately, had a good experience.

Times change. After years of steady-state, property values have gone up substantially. Of course, taxes rose right along with them. Rents have increased nicely, but not nearly enough to preserve ROI.

This year we decided it was time to sell, and everything is under contract and set to close just prior to the new year. I'm doing a 1031 to avoid the brutal tax hit. Which brings me to... building a team (that's what we call it, right?)

For various reasons, I didn't get started on this as early as planned. At a minimum, there is:

1. Find a good agent to work with. Someone who knows the industry and can answer questions beyond just "how much have you got, what do you want?"

2. Ditto for a good lender.

3. An attorney for ownership structure, contract review, etc.

4. Contractors, but I've got some leads there and am not quite as pressured.

5. Ideally, to meet other investors with similar interests who're willing to chat. Naturally, Covid makes this tricky.

We live in the Chicago area now, and plan to stay long-term. I'd like to focus on property within a reasonable driving distance. I'm interested in "middle quality" commercial multifamily. By that, I mean properties which are currently occupied (though maybe not fully) and generally functional, but which have room for improvement. So nothing that isn't livable, but also no brand-new 5-caps in Lincoln Park.

What I'm looking for are helpful tips about making the contacts mentioned above (agents & lenders in particular), and general thoughts about making the step up. Clearly I won't be doing everything myself this time.

Any and all thoughts appreciated, especially from this area. Thanks!