With the new spam regulations coming in, I’m feeling like cold calling might be a thing of the past.

I read the permitting process and it seems somewhat strict.

Not all buildings allow STR due to regulations.

@Maurice SmithRL property management is pretty good they are just very strict on where they will and won't manage.

@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.

@Eric Smith A 1031 exchange with a related party is possible but comes with strict IRS scrutiny and holding period requirements.

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!

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?

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.

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