Between us both still working full time, our 401ks, my 2 pensions, a primary residence 4 years away from paid off, social security, wife’s government pension, her 401, & working full time, with kids out of college & college paid off, we have mutual desire for owning lakefront log cabin.

School districts can play into the desirability for renting so pay close attention when doing your due diligence.  

the area is a desirable area, and not in a park. 

Find out what his needs and desires truly are.

Another consideration is that the renter pool is not as desirable during the winter and your rents may also be slightly lower as a result.

Only way I can get to a $29 principle payment and $1,660/month is with a $140K loan at 14%  Refi is desireable if these are his terms, but I'm skeptical that this is correct.

One that could potentially net you $3,000 per month (approximately) in positive cash flow, to off-set the costs of living in your desired neighborhood with your family.

BP always talks about the allowable unfair advantage in RE of knowing about growth before it is fully realized, and I feel these things make Apopka an extremely desirable market for long term holds especially. 

) - Gross Monthly Operating Income 3,562.50 Monthly Operating Expenses Property Management Fees - Repairs and Maintenance 166.00 Real Estate Taxes 416.67 Rental Property Insurance 300.00 Homeowners/Property Association Fees Replacement Reserve Utilities 180.00 Pest Control (310.00) Accounting and Legal (60.00) Monthly Operating Expenses 692.67 Net Operating Income (NOI) Total Annual Operating Income ( Gross Monthly x12) 42,750.00 Total Annual Operating Expense (Monthly Operating Exp x12) 8,312.00 Annual Net Operating Income 34,438.00 Capitalization Rate and Valuation Desired Capitalization Rate 8.00% Property Valuation (Offer Price) 430,475.00 Actual Purchase Price 400,000.00 Actual Capitalization Rate 8.61% Loan Information % Down Payment 5.00% Down Payment 20,000.00 Loan Amount 380,000.00 Acquisition Costs and Loan Fees 4,000.00 Length of Mortgage (years) 30 Annual Interest Rate 5.800% Initial Investment 24,000.00 Monthly Mortgage Payment (PI) 2,229.66 Total Annual Debt Service 26,755.94 Cash Flow and ROI Total Monthly Cash Flow (before taxes) 640.17 Total Annual Cash Flow (before taxes) 7,682.06 Cash on Cash Return (ROI) 32.01%This is what I came up with 

Petersburg very desirable locations where you can fix and flip or fix and hold/rent.