A longer timeline will make paying the extra 2% now more attractive.

I'd also add to that that you are paying a 20% withholding tax on gross rental income. 

I'm being required to pay another application fee and then $600 application fee to hopefully get this approved by the Board to allow me to continue running the STR that they approved 6+ months ago. 

You don't need to pay anyone to learn.

Best pay compared to cost of living.

Of course you don't want to over pay for land, but site conditions and construction type will dictate costs....is there underpinning?

Am I ok with this plan to ride up the appreciation, mortgage pay down and rising rents?

I could take look at it for you, and help you understand it if it's a standard lease, no need to pay me, although I am not a lawyer.  

The law does NOT apply to landlords:With less then 5 rental unitsThat live in one unit of a duplex and rent out the other unitThat rent out rooms in the home they occupySo, landlords can no longer state in their rental ads, "Section 8 not accepted".The reverse is also true, "Section 8 only", cannot be used.We've always recommended screening S8 tenants the same way as cash-paying tenants.Landlords waiving application fees and/or security deposits only for S8 prospects may also be violating Fair Housing.

We will be paying nearly $50,000/year in property insurance.