First off, welcome to the tank!
Second, I would definitely suggest a 2015 or newer. The Rushmore design is just so much nicer and has a lot of great design/rider comfort features. '15 and 16 are pretty much identical and both have the tried and true 103 motor. You can get some pretty great deals on used bikes from those years and there are a bajillionity accessories available. 2017 was the first year of the M8 motor, so you have to decide if the M8 107 is what you want to focus in on or not. It is an entirely different beast – single cam (103 is a twin cam), slipper clutch, different suspension, and overall a different "feel". The M8s have more available torque and HP through the rpm band, and they are supposed to be a lot smoother – no more "clunk" from the shifter. But there have been some growing pains with the new motor as well. i.e. Oil sumping, warranty BS, etc
There are tons of posts and more knowledgable folks on here that can explain the nuances of each year. Just do a LOT of reading and get out and try a couple 103s and M8s. That is going to be your biggest advantage*– riding! Me personally, I have a ton of time and money invested in my '15 and it is perfect for me. I have zero desire to get into a newer bike.
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'15 FLTRXS - V&H Power Duals w/ Screamin' Eagle Street Cannons - Arlen Ness Big Sucker - BT4180.14 w/Arc Moto 602v2 and Polk MM652 - Le Pera Maverick Daddy Long Legs - Advan Lowers - Freedom Shield 15"