But when it comes to conducting Cost-Segregation studies to “accelerate” the depreciation of a property, can I still “carry over” additional entitlement from, for example, my first tax-year into the following years even if I am not meeting the REPS criteria through STR’s? 

Learning from Others: The Value of Case Studies and Success StoriesOne of the biggest advantages of having resources is that you get to learn from those who’ve already walked the path.

I'm getting married in the next year and starting a family, and we plan to move out when that happens, which means that even if I went through the permitting process now and was granted a rental permit w/the town, I knew that ultimately I was going to find myself screwed when the time came to get a renewal on it (every 2 years), and I wasn't able to prove that the property was still owner-occupied.

There are always parents of students who have failed out, transferred or chosen to study abroad offering discounted subleases every semester.

Make sure to study the buyer your trying to target...but you already know that.Hope that helps 

Take time to study the specific neighborhoods where you want to invest.

Can they prove how long it takes to rent a vacant property?

If you’re curious why - talk to @Michael Plaks :) if you want a creditable source on Congress.gov that proves this - read my post.

Not an economist who has studied these issues, just and armchair intellectual here.I bought a house in my neighborhood and my realtor thought I should airbnb it. 

Maybe someone here can point us to one and prove that print media isn't dead :)