I like the option of putting more down if you’re paying 7% plus interest.

Even though it doesnt cashflow well asap, the potential would be its proximity to Las Olas, downtown and the size of the lot, different development options. 

Perhaps that is an option for you unless you're in a rush to pull your money back out right away?  

Try to narrow down your options to the top 3-4.

Cleveland is a solid option.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.

Our team discussed multiple investment options with him, including new construction homes in nice areas that likely attract better quality tenants.

Other option is to continue down the self storage facility path, do nothing, or list it. 

Here are your options when it comes to financing:a.

Eugene sounds like a great option with the university draw, and Portland has some solid opportunities too especially if you're leanign towards the MTR/STR route.