The most satisfying changes I've made is move out of tech management and back into just engineering roles, I sold my house in the city and moved to 5 acres in the hills where i work remotely for less money gladly, I've paid off everything, and now I have the flexibility to do anything.

For instance, cities like Chicago are known for landlord-tenant laws that skew heavily in favor of tenants, and that risk should be baked into your underwriting.What’s your take on balancing short-term cash flow with long-term equity growth?

There was also a part of that law that enacts rent control anywhere in the state, which may affect your plans.Make sure any changes you are proposing to the contract are compliant with the "new" New York State housing laws. 

The properties are limited to certain areas of the cities.  

For 10 years, every arriving party in my STR finds 1) a fresh bowl of fruit, 2) a local city magazine and a weekly periodical and 3) 2 bottles of wine (1 white, 1 red, 1st bottle is complimentary, envelope to pay for 2nd bottle).No great expense, but "wows" the guests every time. 

Go to Omaha and Sioux city tomorrow for inspections and client meets. 3. close new loan with my bank unsecured ( those babys can be tough to get).4. get my mind ready for 9 grandkids at the house this is the toughest one :)  Patience 5. firm up goals for 25 solidify my new clients that I have gotten in Q 4 24.

My wife and I have loved real estate for a long time and invested in other areas, but are focused on building our portfolio in Kansas City.

You need to research/know the rules, laws and regulations (including HOA if applicable), like you'd do in any US city.

A lot were doing air bnb up until the new rules came in place for the city of San Diego but you can still find a property outside the city that you can potentially do STR with to cash flow. 

I recently purchased a 1500 SF two-story rowhouse in New York with a building class designation of Two Family Dwellings - Brick (B1).