Many landlords will tell you a "good" Section 8 tenant is one who is still working but not making enough to afford suitable housing on their own.  

At this time I am seeing 3 suitable options that I may be able to move forward with to use as a short term vacation rental or long term rental.Option 1: total Rehab of the interior/exterior while using the old foundation (if inspection finds strong/usable) Option 2: total demo of the structure and build a larger house on the second parcel outside shoreland management zone options 3 (combination): rehab/use as ADU and build larger house on second parcel Thank you for the help in advance! 

That would be my first thought.If some of the land is suitable for farming, you might want to look into some of those farming programs where they pay farmers to NOT plant anything. 

The more contingent liabilities you stack up, the more nervous future lenders will become as they consider your suitability as a borrower.

When you do Refinance, the original loan is paid out by the new Lender, and hopefully your calculations about it being a suitable BRRRR deal prove correct. ie. 

@Beau Pearson I will post a property on Zillow but use cozy.co for all the background checks once I have found a suitable tenant I use deposit slips pre-filled out for the bank account associated with that property so far it seems to be working great

The current market environment may not be suitable for entering real estate.

Did you find the deal first and then bring it to this community, or did you establish relationships with potential investors first and then find suitable deals?

Since I am “shopping” remotely, and my timeframe is limited, the odds are good I’ll find something suitable on the MLS.

It's my opinion that land contracts are more suitable for the sale of business and income property.