I would say this is 98% of realtors.

Upon logging into my Stessa account, I discovered that all my property rent rolls, and transaction history from the past two years had disappeared.

This is true regardless of how long you have owned a vacation rental. 

I would suggest starting with reading the IRC book all the way through multiple times.

Quote from @Milena Garcia: this sale I hope is all done after 2 months..

As you read these books, watch the BiggerPockets podcasts.

I have just read through the four years of this thread and found some great tips, thank you to the OP @Thomas Youngman and all the content others have provided.

Legal entities are set up for this purpose.  

Was just about ready to pull the trigger on one of the many courses that are offered out there, particularly Pace Morby’s, but after reading several posts full of reactions to the question “should I join and pay for a course?”

Hope this helps, best of luck!