@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

I believe that you don't get returns (failed to deliver) with bulk mailers so you don't know which addresses are bad.That's the simple stuff.My advice is to do various mailings that you or some prepares locally, that go out immediately, using 1st class postage.

You could also consider house hacking locally.  

probably a wholesale company.. get a second opinion from a local RE agent so you dont get hosed. 

It’s crucial to have local market knowledge or work with someone who does.

Hopefully, this is a useful example of what’s achievable with out-of-state investing, even with no local connections. 

For starters, I recommend to begin with a single family home or if you are looking to start locally, do house hacking. 

Just be sure to check local regulations because some spots are cracking down on STRs.

Right now there's huge concentration, but as this continues to build out and we see north of the high 30s GW by 10 years from now it'll be almost a requirement to keep some type of locality based risk assessment and to diversify. 

I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.