and I spoke with the bank earlier today and confirmed that we should qualify for a jumbo loan that would allow us to make this work out.The place I am getting stuck is trying to figure out any kind of realistic estimates for whether the three cabins are actually able to generate enough positive cashflow to allow us to eventually step back from our jobs and/or running the numbers for everything in a way that I would feel confident enough to try commit to something like this.Would it make better sense to try and start out with something more simple/conservative?

@Sitaram KoppakaIn addition to speaking/researching the local city/county assessor’s tax office, you can reach out to a tax consultant and often get a good faith estimate for the expected change.

Therefore increasing the cash flow.I know this is a rough estimate as more information is needed.

If they have an estimated damage in the report it is a pretty wild guess by a Fire Marshall who doesn't estimate for a living. 

Zillow rent estimate shows this place at $850/month.Someone will buy the house and spend $15K to fix up the place.

I realized I was running out of time on my contract and had no contractor contacts to bring in for estimates on repairs which is what made me so unsure and killed the deal.

The conservative way to budget Capex reserves is to look at estimated remaining useful life of each item: roof, siding, windows, kitchen, HVAC, water heater, bathroom, fences, gutters, chimney linings/tuckpointing, foundation items, etc, and assigning a replacement cost divided by remaining useful life.  

They will also provide renovation estimates and the other information you will need in your evaluation.

If the OP's estimates are correct AND they're in a fast-appreciating area, it might make sense to hold it.

The information below was provided by a Loan Officer for my Closing Cost as the Buyer/Borrower and Title Company for the Seller's Closing Cost.Loan Information$185,000 = Loan Amount$9,250 = Conventional Loan Down Payment (5%)$4,980 = Estimated Closing Cost: (Processing Fees, Underwriting Fees, Appraisal, Appraisal Review Fee, Title Insurance Services, Settlement Fee, Administrative Fee, Courier Fee, Owner's Title Insurance, Lender's Title Insurance, Recording Fees, City/County/Stamps, & State Tax/Stamps)$2,120 = Estimated Prepaid/ Estimated Reserve Cost: (Daily Interest, Home Insurance, & Property Taxes)$16,350 = Total Cash at Closing from Borrower$1,000 = Estimated Monthly Mortgage Payment: (P&I, Hazard & Mortgage Insurance, & Real Estate Taxes)Seller Closing Cost$0 = Agents Commissions: (No REA involved in this transaction per Seller's request)$900 = Total Cash at Closing from Seller: (Estimated Doc.