I'm also considering a separate living room space or maybe some kind of artist studio. 

Now that i have  to sell, i am trying to see if i should sell each unit separately (each has a PIN) or as a whole.

It's a good little loophole for a short-term rental of your home, including renting it to your own separate business.

First you need to learn to separate the following:Maintenance: usually things related to wear & tear or tenant damage.Repairs: usually broken items like doors & windows, caused by tenant or nature.Capital Improvements: usually expensive things that wear out: hot water tanks, furnaces, roofs, etc.The seller is correct that Repairs & Capital Improvement items should not be a factor for awhile (ALWAYS get your own inspection to confirm).

Out of bed before 5 am - (I had a separate habitat for starting the day right but then slowly started pushing my time of getting up back2. 

We have a few properties that are held as JV's in separate LLC's and just want to make sure all is above board.Thank you, and Happy Holidays! 

Separate the work into 3 separate categories: 1) Those that are specifically related to the future STR usage, 2) Those that benefit you while living in the house and have zero bearing on the future STR, 3) those that benefit both you and the future STR....assign a percentage to the usage.Be specific and complete.

This won't change the numbers at all, but it will correctly reflect the personal ownership of the RV.Since the RV is in our personal name, and our two LLCs use it for travel, should we treat the RV as a separate rental business (sole proprietor) and rent the RV out to our LLCs when needed for travel?

Luckily both sites collect the taxes for our place.Our little town did implement a 1% tax that I have to pay separately.

It may be more helpful to put some of your specific questions right in a post or separate posts.