Many people lease for the summer months (July-Sept) at 4-5X normal rents (up to $10k during sailing events, tennis tournaments etc.), then cut the rate for off season months to Salve Regina students, or Navy on extended TDY /training.

I’ve locked up a lease option on a small commercial property and the house behInd it, that’s been vacant for five years.

Your list is pretty comprehensive, I would check deeds, title, leases, management agreement, vendors, etc.I tend to disagree with the bolded portion though.

Is there any value in trying to lease option it? 

I have done some flips and lease options along with a few rentals.

I'm in the process of breaking my lease and moving into a recently purchased SF home.

To help clarify, Loftium has both our down payment program available in Washington state, and our Loftium Lease program where we offer landlords above-market rent and place long-term tenants who manage Airbnb guests in part of your rental property. 

If you have a clause in your lease about not making any changes to the property I would use that to get the pool removed.

I've done assignments with Lease options but never a subject to. 

If so, leasing it out and buying a new one could be a great place to start, if you're looking for rentals.