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. 

Any of the above kills the STR loophole under this "substantially all work" option for material participation.Is there a way to qualify if all my outside help was a cleaning lady for 2 hours?

Annual fee of $1,000, no other payment options. 

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.

If you ever want to talk strategies or options feel free to reach out I can go over some loopholes and tips.  

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

The options we have are: - Do nothing and keep monitoring the crack.- Seal the crack only from above and hope it stays static.- Stabilize the foundation with helical piers on the exterior. 

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

Also, when it comes to these infrastructure items you are concerned about, learn more about the "options".

Ozaukee County would certainly be in my immediate plans, Milwaukee would be definitely be an option in the future.