Without pre-arranged terms, its not a toss up whether the sellers "care" about your situation.Like I said, its really a matter of how bad do you want it. 

I am researching the market and will start diving deep into cleaning arrangements, repair folks, what types of properties bring the biggest return (size, more private vs more crowded cabins, closer to or further from town, hot tubs, views, etc...) 

I’d still recommend at least monthly though so you’re not hit with a huge tax bill at the end of the year. very helpful, thanks a lot. i would definitely make better arrangements for 2023 just working to fix the 2022 situation. 

Once you've established this arrangement, you can repeat the process or search for another investment property.

It makes us stand apart from all the other "I Buy Houses Guys"I suppose the 85K that we made was worth it...If anyone wants one mailed to them.. that can be arranged, just let me know.

OK, all assumptions of my understanding of what is fun or your little witty barbs directed at me are irrelevant to the point...or any of the exact facts/details being incorrect do not negate the principals I am using.you want to be MR.super-2A amabassador- RSO-safety guy with some strangers you don't really know, despite that not being the primary objective of your arrangements....go ahead, nothing could go wrong...it's that sort of thinking that experiences a higher level of hard lessons learned in life. .I am not a lawyer, this is not legal advice.

The new tenants are going to have time to qualify, arrange funds, give notice to current landlords, arrange time off, etc etc. 

Apart from the downsides mentioned above, one thing to look into would be the additional work it will take to manage your tenants, because in this arrangement there is a lot more potential for tenant drama. 

Would like some advice on pro's and con's of deciding whether to have a long term agreement or Airbnb style arrangement for a propsective tenant who's willing to stay long term in a guest room we have at our place.

My 16yr old daughter works there as a server and I could arrange the upstairs room.