I'm currently working with an estate planning attorney and she said she said we could put the LLC in the Trust but said she was not the best person to advise on the pros and cons of that and that we should talk to a business law attorney.

Yeah the law changed I believe back in 2020.You cannot do short term rental with an HPR unless you own both sides.   

I think hard money lender to take this risk cannot legally charge appropriately which means the law is working against you (the law meant to protect owner occupied owners from unfair loans).I agree with @Jay Hinrichs that your best option likely is to sell on the mls.  

They are designed particularly with mother-in-law or next generational living in mind.

Hi Anthony-You asked about the best ways to find off-market deals for your in-laws to buy and move into and you are focussed on the Santa Barbara, CA area which I have been to and it is gorgeous.It kind of reminds me of an Ann Arbor on the ocean. :)Anyway, I like your strategy of driving and looking for houses in need of repair and sending handwritten letters and contacting rentals for the reasons you gave.

Maybe the AI can keep you from calling people on the no call list and violating the law?

A single-family home or small multi-unit property can be a great way to dip your toes in the water.Build a Team: Even if you’re planning to handle most things yourself, having a good real estate agent, property manager (if needed), and a reliable handyman can make life so much easier.Learn the Local Laws: Pensacola is pretty investor-friendly, but it’s always good to know local zoning laws and short-term rental regulations if you’re thinking about Airbnb or VRBO.Run the Numbers: Make sure you’re clear on the property’s cash flow potential.

If your company were to manage the STR in CR how do you deal with matter of safety / home burglaries? 

The government and HOA's favoritism toward big companies like Sonder.People will keep say the issue is saturation.

What we did was open a holding company, and the LLC that owns the RE and management company under that.