And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

I’m also an active member of the local landlord association in Joliet (JRLA), which has been a great resource for networking and education.

@Dan Geffen moved down there and knows the area well if you want to connect with a local investor.

Nonetheless, it was made possible by a local credit union.

About me, most of my assets are RE but in another market so I would be diversifying in that market.Potential for appreciation is very uncertain: prices have risen a lot locally lately and are as high as they have ever been, and it’s unlikely higher prices would be affordable by locals.

I would also join your local Facebook pages for investors. 

The last one, however, started with many people from two certain neighborhoods, gathered by a local non-profit, who spoke much about affordable housing, being displaced, etc.

There’s huge retal income potential if you nail that balance between improvements that wow tenants and improvements that merely look fancy but don’t justify higher rents.I’d also keep an eye on how your high end plan fits the local demand.

Consult a CPA or real estate attorney to understand tax implications, build a reserve fund for unexpected costs, and research local regulations to ensure a smooth and profitable transition into rental property ownership.Good luck!

My only recommendation is you go with someone local to where you are.