In Berlin, rental arbitrage has been very profitable, with average annual margins of 25-40% after all costs but before taxes, so shifting to a market where arbitrage is barely breaking even is definitely a reality check.Given your experience, would you say the best way to enter the market now is through purchasing properties with financing?

Here is a list of the Chicago events on BP: https://www.biggerpockets.com/forums/517/topics/1230201-look...You are definitely on the right track.

To avoid reducing your lifetime exemption, you could gift equity incrementally, but this requires proper legal structuring (e.g., fractional ownership transfers).

Don't have answers, but definitely following this thread!

You can definitely refi your current home into a DSCR loan.

BP is a great place to definitely learn and connect with like-minded people. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Access to a heloc definitely makes more sense if you are doing a BRRRR strategy or flips, but neither are a sure thing.

I definitely think co-living would bring in more revenue but also more work. 

If you have the budget for repairs if you rent it out, definitely rent it out!