When you get mid-term rental inquiry from booking platforms (like for 28 days, which doesn't turn guests into actual tenants), what steps do you take?

Might take a few tries but you'll be able to connect with one.  

Beyond the Monthly Management, Placement & Maintenance fees, all other fees in our contract are IF EVENT -> THEN fees.

Anyone know how long it takes for the city to approve so that the slab can be poured? 

Take that 40% hit.

But I will take my chances.

So it could take a decade to get to todays market rent. 2) it’s almost impossible if not impossible to non-renew a tenant, especially if you’re not an owner occupant. 3) As a seller, even if I could remove paying tenants I never would without a non-refundable payment from a potential buyer that covers all vacancies for 6 months if they fail to complete the purchase. 4) You MIGHT say as a buyer that’s worth it.

My advice is to keep trying because all it took was to find the right smaller bank willing to take a chance on me. 

Also, take a look at a condo if you really want to be in SB proper, it might be a way to get started, and calculate the insurance and maintenance that an HOA would pay

Even with all that it could burn down.