So I'm looking for some advice as I begin this process- should I drop the agent and pursue the tax address I found first? 

Below are some quick tips about cash out refi vs HELOC/LOCCash out Pros-tax free money-low interest rate-fixed monthly payments unless you choose a variable productCash out Cons-closing costs (couple thousand)HELOC/LOC Pros-tax free -its a line of credit, hence you can use pay back then use again-usually NO closing costs on residential Helocs; there will be closing costs on commericial LOCs-commericial LOC is very fast moving as far as getting funding and refinancing  (Makes it easy to rinse and repeat)HELOC/LOC Cons-higher interest rate-variable rates-monthly payments depend on amount borrowedHope this helps,CB

Madison County does come to inspect short term rentals and also a tax(es) of 11.75% applies on rentals less than 90 days. 

Seller has not had to pay taxes in years since it’s currently zoned as AG1.The property has been Pre-Approved Rezoning to Allow for Sub-Dividing and Building 2-4 Homes.There is currently a single family home on the property there now, built in the 1950s, but will have to be torn down.

Seller has not had to pay taxes in years since it’s currently zoned as AG1.The property has been Pre-Approved Rezoning to Allow for Sub-Dividing and Building 2-4 Homes.There is currently a single family home on the property there now, built in the 1950s, but will have to be torn down.

Though the city needs a lot of work in terms of crime and school, there aren't too many small/mid size cities with the arts, food, nightlife, access to suburbs, lakes, wine region, etc. that Rochester has while having extremely low taxes. 

I've read through the contract and will summarize here with simplified numbers (not the actual numbers) what I believe the contract says and follow up with some questions for you more knowledgeable members:1) Purchase Price: $100k2) Initial Down Payment: $10K3) Buyer pays seller monthly payments based on 30 year amort of 90k at 5% which is $484/month4) Remaining principal balance to be paid off on the defined Closing Date (roughly 2 years from now)5) Buyer pays taxes and insurance6) Buyer to provide Seller a Loan Commitment from a Lender on or before the Closing Date7) Seller will transfer Deed when Buyer pays full Purchase Price8) Buyer will pay the Seller's existing monthly mortgage payment that exists on the property, which is $100/month, directly to the bank.

Properties within 1-2 miles of each other will get different tenants, have different tax rates, be in very different neighborhood classes that are experiencing very different levels of investment and development. 

No Income/Tax/Employment documentation whatsoever.

I can also just withdrawal the contribution amount and avoid the penalty and tax.