Hi @Evan Coopersmith - Even though you aren't currently interested investing in Chicago I'd still suggest looking into some of the local meetups here! 

Unethical practices: There are reports of agents coaching buyers to avoid properties where commissions aren't pre-set by sellers.

The seller should not be expecting you to be the buyer, or surprised when you aren’t. 

This way, they get the cash they need without selling and without triggering any taxes since loans aren’t considered taxable income.

If you’re looking for short-term cash flow, you might need to explore nearby markets with lower entry costs and higher cash-on-cash returns, even if they aren’t as familiar to you.

For those who have applied and don't meet criteria, what is the best way to communicate that you aren't moving forward with them that does not risk violating any fair housing rules? 

Since you are new to the market, you can look at what the top rent pulls look like and cater accordingly on the design.You always want to build relationships with contractors, but that takes time and you always need a solid bench, just like in basketball because some days your starting plumber just doesn't show up and you need to bring in the backup.The rates are the rates and they aren't going way down soon so it's just part of a different metric to evaluate in your new market.Good luck!

Just keep in mind that entertainment expenses—like taking clients out for a show or a game—aren’t deductible anymore.And, yes, you can deduct 100% of your education expenses if you’re already a real estate investor.

The landlords aren’t staying silent either.

Quote from @Miguel Del Mazo: Knowing more about the area, it sounds like you'll have an ideal avatar of wealthy, young and trendy professionals that aren't ready for or looking for a home to own.