Is it too late to expand?

[Lisa Peck]

Hello, I'm old and new to investing in Real Estate.  I have been a Real Estate agent for almost 27 yrs (IL and CA).  Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well.  Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so.  Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here.  We manage them ourselves (from afar) since we already have people we trust there.  I'd like to add a small multifamily (2-4) to our portfolio next.  We live in SoCal now and find it difficult to find anything here that pencils out.  I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC.  I've never been to any of these places.  I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations.  I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside).  I've been listening to Dion McNeeley lately and find him fascinating.  I really like his desire to be as efficient as possible owning as few rentals as necessary.  I'd love any input!

[Jonathan Klemm]

It's never too late to expand @Lisa Peck!  

You can still find that unicorn mix of appreciation and cashflow right here in Chicago!  Some of our near suburbs in the west like Cicero, Berwyn, Oak Park, River Forest are great for those.

Also, some of the South East Chicago neighborhoods are for sure on the up and up still like Washington Park, Bronzeville, Woodlawn, etc.

If you have a solid team here I suggest digging deeper in to the market...I am, of course, biased and everything you said is true on taxes, tenant ordinances etc.

Happy to discuss more if you needs some boots on the ground input.