I inherited a condo in a popular tourist town that I rent out through VRBO. The condo is furnished with many antiques and valuable pieces of art, some that came with the place, and some that I picked up at estate sales. In two years of renting, I have had no theft, and the only breakage was after I broke my own rule & let someone with a toddler stay there. Here's what I think contributes to my success:
--I primarily market to couples, not families. I do not accept children under 13. I do accept dogs and have found dog-owners to be very grateful & responsible renters. At least one renter must be over 25 (most are baby boomers). I limit the condo to 3 guests, max, and price accordingly. Other owners with my layout list their condos as "sleeps 6," calling the room I call a study/guest room a second bedroom, and having a sleeper sofa in the living room. The larger the crew, the more likely you are to have damage. I do not try to squeeze every dollar out of the place. After only 2 years, I have many repeat renters and my calendar is fuller than those of the "sleeps 6" people.
--I removed anything that I felt I could not bear to lose. Anything I'd be heartbroken about is in my home or in the locked owner's closet.
--I treat all renters with respect and have gotten that in return. I, or my great, well-paid cleaner leave a personal note and a welcome basket of wine & snacks for all guests. I have several pages in my info book explaining what all the art is & where I got it. I thought this might encourage theft, but so far I've just gotten nice comments about the art & one request to buy a painting should I ever wish to sell it.
--I began by requiring all renters to buy VRBO's damage insurance (up to $5K insurance for $99), but I've ratcheted back to a $200 refundable damage deposit, and have never kept any of it.
--You do need to remove personal items like your toothbrush and pajamas. Renters do not want to work around that stuff, or around your clutter. The owners closet can hold these things.
I think your cabin sounds like a wonderful and important part of your life and history, and something you do not need to give up and can make work for you financially as well as emotionally and recreationally. In the future, it can be a place where your kids gather, where you & your wife can be for long stretches while you rent out the primary home if you wish, or after the kids are grown, you may feel great with a small primary home plus the cabin. Keep it!