Large tree in back is dead .

My husband is a physician and we have a couple homes, stocks, other investments, etc. 

I don't like stocks etc.

The guy that turns on and off the lights in the P&G lobby has a couple million in stock.

If so you could run the numbers on taking a loan on the zero-debt property to pay off the other.I'm still unclear on the goals - you've brought a lot of other things into the equation (e.g. paying of high interest debt, STR as personal vacation home, stocks/dividends, etc.). 

His family made their money with W2s and the stock market.

You need a repair partner who can get out immediately and has quick access to replacement parts (if not already in stock). 

The hilly terrain is a main reason for this and you can't really see that on a map so knowing the areas is key.We have old housing stock as well so big things like plumbing and electrical can vary cost wise if they have or haven't been updated.

You’ll want to make sure your property is styled and stocked to fit the target market catering to what Big Bear has to offer and what guests expect.

I told her no and then she told me to sell my crypto, sell my stocks, apply for credit cards and offered me financing.