Don't take my word for it though.

In other words, to maximize tenants seeking to rent, what are the best months to have lease end?

Guys have heard that ad nauseum and its now a code word for "Do it cheap".

I've largely stayed away from the "sub-to" buz word, but I have done a couple sub-to flips knowing that I only needed to hold onto them a couple months and I was prepared to pay off the notes if they were called.Sub-to for long-term hold on the other hand has me nervous. 

Alas, this scenario didn't last very long, as you would expect in a free market capitalist society -- new money flood in, more STRs in supply, property prices increase, STR incomes decrease, until a new equilibrium is achieved.Nowadays, the word STR is being used to describe both the property and the business.

They tell you you’re asking too much rent (you lower rent, avoid vacancy and make more money) ,your marketing is bad (they take new pictures, advertise in different places, change wording, whatever, and get a tenant saving vacancy.)  

Any advice, tips, words of wisdom I am open ears!

A positive word from you could turn things around here where people are beginning to feel the course is a scam.

You have uttered the words that act like a whistle for the Pied Piper so I will get out ahead of it.

Quote from @Rud Sev: Sorry @Sean O'Keefe, I shouldn't have used the word "gain".