If you meant co-living, look up @Grant Shipman, that is what he does.Can you please explain or point me to a post that tells us what your model is?

You may be safe to get non-commercial F/F adding up to 2 ADUs to a duplex even though by rule this does not qualify (in my area I have never heard of this being an issue). 

Foundations actually don't come up that much in Chicago.... so many awesome brick properties.

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

I can feel that you have embraced the move and change. if you want to meet some local investors there is a meet-up next Tuesday. it's posted in the classifieds.

You may want to find a good agent in the southern NH area as I'm hearing that market is prime for investment with people moving up from MA, but your other markets might be just as solid.Also, since you're already an agent, it's pretty easy to get your reciprocal license for NH or RI.

Everyone has a story, don't get caught up in their story.

Screw up an investment and you'll lose the money and the relationship.

Local PM here - we have multiple development projects we are gearing up to sell, both small multifamily and townhouses should you want to take a peak at them.

This means that the bulk of the expenses are not going up annually.In addition, if OO you get to write off the property tax and interest to the SALT limit ($10K).