All the usual Lease prohibitions against running a business do not apply.

Custom cages can require long lead times and may be cost prohibitive, The more attractive (less like bars) the cage is, the less buyers/tenants may question the neighborhood. 

The approval letter from the seller’s lender is for Only the buyer name on the purchase contract, no assignments and double closes are often prohibited. 

As I wrote above, conveying title to the land is not prohibited by a title policy, whether the Grantee will be an Insured under the existing policy depends on if it meets the policy definition of Insured.

I've read a lot about these tools, especially the prohibited transactions.

Defiantly hope the town agrees to it , I’m not trying to create anything ridiculous, but I think sprinklers would be cost prohibitive, and additionally difficult as one of the units is rented. 

I am going to follow your advice and seek out a CPA and/or a CFP, as well as an Attorney, provided their services aren't cost prohibitive.

All is well till the local authorities prohibit their STR or a bunch of people start STR'S in your location.

The zoning prohibits more than one structure.

So, what you're saying is, you really want private (non-company paid) health insurance, but the cost is prohibitive?