Is this something you have experienced as well, how did you deal with it?

As a general rule I would say multi for all the reasons people listed.

There are a few people that would be wise to reach out to in order to get this information.

This is a great place to learn and to connect with people so take advantage of all the great resources.

For some people this is OK since they will get use, future appreciation and a likely refinance in a few years. 

Any advice on the kinds of people I should have in "my team" to make this a success?

They dive deeper into niche services by providing in-depth analysis from a high-level and experienced point of view.I see your biggest obstacles as a lack of experience and background as investors and the perception that these are services your wife should already be offering as the licensed agent.Given those obstacles, what differentiates your service? 

Now you've lost 4 months of rent you are UNLIKELY to ever recover:(So, yes, hire an experienced landlord-tenant attorney.

I would just say that recently in my experience diversifying out from STR into motels/boutique hospitality has been high risk and set some people off path - it can be a very lucrative and good move - however, if you are having a lot of Success with traditional STR - it seems like a lot of people are looking back and saying they wished they stuck with that and expanded with what was already working!

If you really want to sell to people from San Diego then I would just recommend you get your real estate license in whatever state you plan on selling real estate out of.