STR markets are tough and change fast, best of luck!

Not every investor profile fits the SF market. 

Your contractors, staff, and the financial markets will create challenges. 

@Grant Shipman Great stuff, I'm a big fan of co-living/rent by room strategy, and I do it here locally in Denver metro, and it is the best strategy in today's market for any house hacker to live for free or make money while living there, but they have to sacrifice personal space.

What's your recommendation to market it?   

There are a ton that solely focus on those specific markets. ( they do meet-ups, etc. )WOW, AI?

Pensacola is a great market for investing and the number of properties available right now is up so there are actually some on market properties with potential. 

For example, should we focus on acquiring one high-quality property in a strong market, or would it make more sense to spread the investment across multiple lower-cost units in emerging areas?

Once you learn how to generate leads, marketing, negotiating, etc you can go be a solo agent.

Use a quitclaim or warranty deed to transfer the title, and be prepared to pay Chicago’s transfer tax, calculated at $7.50 per $1,000 of the property’s fair market value.