As more people placed more properties in STR inventory, and as more municipalities taxed and regulated the industry, the profitability of the overall industry has reverted to a much more aligned (lower) risk adjusted return.  

Apparently, local jurisdictions here are saying they want more affordable housing, but in the same sentence will also say that there will be more regulations, more environmental protections, and more hoops to jump through to develop starter homes. 

Now, I’m looking at Florida, but it seems like most investors are focused on buying instead of arbitrage.I’m aware of the zoning regulations, but I’m curious—how easy is it to find landlords in Business and Tourist zones who are open to leasing for subleasing?

@Derek SoohooIf you're looking to invest in multifamily properties in Chicago, start by researching different neighborhoods to understand rental demand, property values, and landlord regulations.

I’m based in Tampa and run Graystone Investment Group, focusing heavily on helping (out of state) investors find and manage properties here in Florida.Totally agree on the importance of understanding those short-term rental rules in Florida—each area can feel like its own little country with all the different regulations!

Since you’re managing a Section 8 tenant and taking over property management, focus on understanding local regulations, lease terms, and effective tenant communication.

More effort should go into enforcing existing permitting laws and cracking down on unpermitted work rather than imposing costly regulations that push property owners into avoidance tactics.If the goal is to improve fire safety in Worcester’s aging multifamily housing stock, the best approach is to encourage full renovations that bring buildings up to modern safety standards—not to place additional financial burdens on responsible owners.

I have to check on codes/laws/regulation, but I know CA is on a high of making thinks convenient to build those at the moment.

Next is regulations, checking with city to assure it's legal to do. 

Combined with the changing regulations following the NAR settlement, many real estate agents are leaving the industry.