Recently, NYCHA/Section 8, HUD, and HPD have begun to push several regulatory and compliance initiatives.

The days of banking on vacancy-based resets or buyouts as your core strategy are gone.The deals that still “pencil” tend to look like this:You underwrite long-term stable yield, not big upside.You assume minimal rent increases (or none).You price in legal/operational friction.You negotiate hard because sellers are fatigued and there are fewer buyers willing to take these on now.You diligence each tenant’s regulatory profile—not just lease terms, but age, household makeup, income certifications, and historical registrations.If you go into this expecting returns of 10%+, it will look terrible.

The measure the size of each bedroom and determine the maximum number of warm bodies that can sleep in them.

What would be interesting, is if you placed in the body of your Airbnb description texts something like:  "Please be aware that Airbnb assesses a 15.5% service charge on all reservations, which is then included in your total price."

This can result in misleading listings or poor decision-making, especially when dealing with complex transactions or regulatory compliance.Moreover, ChatGPT cannot ensure adherence to local and state real estate regulations, including fair housing laws, and may produce content that inadvertently discriminates based on race, gender, or other protected categories.

Areas like Ocala, Lakeland, or Deltona are still relatively affordable, and you can get solid rent-to-price ratios (1% range) with less regulatory headache than in bigger coastal markets.If you’re open to moving, though, Greenville, SC, and Knoxville, TN are also worth serious looks.

@Bill GulleyWhat regulatory agency has jurisdiction for registering HML that you refer to? 

So, while California offers many opportunities, high entry costs, regulatory uncertainty, and limited new development make out-of-state markets like Massachusetts a practical way to start building cash flow and equity sooner, while still learning the ropes. 

There are very few qualified intermediaries that have any kind of regulatory oversight.  

Purpose: Assess their grasp of regulatory/compliance and their ability to package deals properly.How do you ensure a loan file is compliant before submission?