For those following along at home, that language is found in Title 10, Chapter 1, Article E, section 6 (or 10-1E-6) in the municipal code.It reads: "The renting or leasing of real property for residential occupation for periods of time less than thirty (30) days is prohibited in any zoning district within the town, except as permitted in this title for hotels, motels and bed and breakfast inns."

So where you'd save a small amount on UW fees and perhaps cross collateralized title fees by doing a blanket loan, you will lose all that savings and more IF you ever decided to refi/sell one without the other... just a heads up.The other issue here is you say your assets are tied up... meaning you have no liquidity? 

I would say that it is a very good assignment agreement as far as non-state specific or Escrow / Title specific.

Definitely find another title company.

Scenario 1: 5/1 ARMRate: 5.675%Monthly Payment: $5100Prepayment Penalty: 3/2/1Closing Cost: Broker Fees: $11,016 (1.25%)Lender Fees: ~$2,000Loan Fees: $600Plus standard title and other feesScenario 2: 30 year fixedRate: 7.375%Monthly Payment: $6086Prepayment Penalty: 5/4/3/2/1Closing Cost: Broker Fees: $11,016 (1.25%)Lender Fees: ~$2,000Loan Fees: $0Plus standard title and other fees5/1 ARM looks attractive but not sure if that's what other people opt for that for a STR property? 

**Title Search**: Conduct a thorough title search to ensure there are no hidden liens or encumbrances on the property.5.

My bank and they would loan me the money if they put somebody else’s name on the title of my house.

before even finding a buyer, I’m pretty sure first you have to find a good title group or real estate attorney that will do your paper work and contracts, and provide you with insurance if something happens later on. 

Might not be a problem with a contract for deed sale as you will keep the title, but best to be transparent with your current lender. 

Go through a title company?