My name is Max Nelson, I am a Bay Area based Investor with a single Family home in Santa Cruz, CA that is a Short Term/Mid Term Rental and a Duplex in Bend, Oregon.

If you haven't already, let me know if you want to look at any cash-out refi options for your short-term rental.

Some options that might be viable for you include: Private Lenders – Such investors usually offer short-term lending but provide greater flexibility compared to a traditional hard money lender.Lines of Credit – Another alternative could be an excellent option to finance several deals at once using a business line of credit or HELOC (if it applies).

My lenders know I have other financing options, which I believe helps me get more favorable terms, but also, helps me to find the best deal. 

My name is Adam King, and I am an avid real estate investor and life long San Diegan!

It's easy to get stuck in analysis paralysis - the key is creating a strategy that aligns with your goals and lifestyle.Then, you can start defining what an ideal investment property looks like in terms of returns and property types, allowing you to evaluate opportunities that fit.Good luck!

Long-winded post, but I hope that this helps others.  

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

Looking for guidance on the best way to proceed going forward in terms of asset protection and how to structure all of this real estate… 

The last point that I would make is you need to get into 3-4 pillars of the business that you will have for the long haul of real estate.