This is the language for time-sharing in the CCR:The term "time sharing" as used herein includes any agreement, plan, program, or arrangement under which the right to use, occupy or possess the Unit, or any portion thereof, rotates among various Persons on a periodically recurring basis for value exchanged, whether monetary or like-kind use privileges, according to a fixed or floating interval or period of time for thirty (30) consecutive calendar days or less.I think the verbage "periodically recurring" is key here. 

Look at their rates, look at their calendars, and make an educated guess.There are paid services like Mashvisor, AirDNA, or LearnAirBnB.

I have been researching different markets, have used Air DNA, and have been looking at current STR availability calendars just to get an idea of occupancy rate but am interested in what your personal occupancy rates are (peak season vs. off season) & the location.  3.

Your filling his calendar with work is better than him needing to quote 5 new jobs to get one new one.

Otherwise I'd go poke around on AirBNB etc. and see what 3/2 houses seem to command the highest prices and/or most booked calendars and suss out why.

VRBO/Homeaway/ AirBnB is the best resource for vacation rentals as you will be able to see live rental rates and occupancy rates by checking the listings availability calendars. 

Your calendar looks pretty booked out over the next 3 months but I'm curious what it is over the course of a year in a place like Gatlinburg.Do you carry loans on them or own them free and clear?

In fact, my past 3 closings have been on-average less than 7 calendar days from the time the contracts were ratified.- Typical REO closing companies do a lot of business these days, and in my experience, it's not uncommon to sit in a waiting room for 2 hours waiting to sign your documents on closing day.

So, since he's paying the entire rent with his booking, we have to get what he wants, and it will go well with all our other guests too.I have one cleaning person lined up but I need to get two more so I can throw out jobs to at least two on Properly and let them "fight" for it.Otherwise, its just a matter of getting those first reviews.How do I explain to guests, before they stay, that certain renovations are still on the calendar, just not happening right now? 

My lease states that guests may stay for up to 10 days and no more than 30 days in any calendar year.4.