Total added renovation costs $25,000.Obviously not optimal, and my first major hiccup in the state.  

I will solve it to the best of my ability, but I don't expect optimization or perfection, only that it is repeatable and reproducible by many people in many lifestyles.

If you want maximum returns for a small cabin under $300k, buy one in the Smokey’s TN and vacation wherever you want with your optimized returns. 

Most companies plan their balance sheets and long-term initiatives this way through a process called capital structure optimization.

If you want deals off the mls you would better to optimize your business so you can buy at higher margins.

The best way to find them is to send out mailers.Some good lists to target are Absentee Owners with Equity, Seniors with Long-time Ownership and Homeowners with Low Financial Stability Scores.You can work with a list broker to optimize your list for your area.

Travis and Nathan have covered everything else, but let me just add that with commercial, you can show an investor the income/expenses as they are currently, and as they might be if the property was optimized.

This may be naivety on my end, or my undying optimism, but how can we make this a win/win?

Not at all giving credit to market timing.2) AirBnB/Short term rentals rule the world crowd3) Realtors who think they run the show in some markets, and also think they "too good" to hustle for some clients because they have had some success in an extended sellers market4) Contractors that don't return calls or deliver on time/on budget (I will give some slack here because demand has been crushing and skilled labor has been short, but I'm looking forward to a balanced market)While I don't personally wish financial misfortune on anyone, I am looking forward to watching housing that belongs to overextended short term operators go back on the market at a discount because the "investors" underwrote it to only perform at optimal short term rates/occupancy.

But also that value jump is significant and a cash out refi could provide the funds to help you both optimize this, and, get another.