@Mindy Jensen - Wasn't there something about how "Adding more people to title" could boost the primary residence cap gains exclusion from $500K to higher number?

The extra cost to do two separate loans will be worth it, especially if you do not want to be stuck with the loan for a long time. 

Between the equity on the condo and the extra cash you have, you can purchase 2-3 homes. 

As an example, we decided to replace the windows in a house we were renovating and ended up costing us $50,000 extra because we got into issues with permitting and suddenly found ourselves having to hire an architect, speciality contractors, etc.  

I'm in the Tampa Bay area and I will put an ad on Craigslist, Indeed or post in a group on Facebook for AirBNB/STRs. 

This added demand for rentals drives up rents.You must invest in a city with significant and sustained population growth to achieve rent growth that outpaces inflation.

Maybe adding a camper spot as well?

They’re built for heavy use and have faster drying times—usually 30–45 minutes—without needing major electrical changes.If you’re up for a bigger investment, adding extra stackable units in the garage could be a great long-term fix, though it’ll mean some electrical work and setting up proper ventilation.I’d probably go for the commercial upgrade in your current space first—it’s quicker and might solve the bottleneck right away.

It would also have to be put up and taken down between each tenant and I don't know how responsive your PM will be to this extra work. 

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work.