I’m looking at purchasing a quadplex in New York City, where all four units are rent-controlled, with two units vacant and two still occupied by rent-controlled tenants.

I glanced, and I saw that Wells Fargo and Citi Simplicity have a 21-month offer.   

Not sure if this makes the city less favorable to landlords. 

I think initially it makes sense to find properties that already have finished basements, in-law suites, etc. as converting those spaces to ADUs will be inexpensive and create a significant amount of rental income ($2,000/month+ in most areas close to the city).

Yes, Scott Galvin with Keller Williams Partners is amazing and has been an expert in the Kansas City Marke for over 3 decades.

I have used them in the Panama City, FL area.

Buffalo is predicted to be #1 2025 Small City Housing Market of the year.

My wife (she picks all our STR stays) would not rent a STR in that type of area in any City but we are not everyone so take that with a grain of salt.

What is it like investing in Birmingham?

House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.