There's no "right" answer to your question. I have a 2011 Roadster with Lush components and a 2020R. They're very different bikes and, therefore, I struggle to sell the Roadster. I see no advantage to getting a 2018 model IF you want to go the 2.3 route. There are lots of older (same, same) models (ABS being the major difference in later years) with low mileage to be had for $7,000 or less. But if money is no issue, then the question becomes what's the difference between the two bikes. The 2.3s have a more classic analogue feeling to them. They are less refined. Potentially equal in torque and power if you have upgrades, stop slower, and are less nimble. The 2.5s look and ride like a more modern bike, with lots of electronic "stuff" (stuff that I worry will go wrong and I won't be able to fix). Stop faster, corner better, and have less of a stealth factor. By that I mean most people don't know these bikes and if you pull up on a 2.3 in a group of bikes they will most likely be very surprised when you leave them in the dust. With the 2.5s it looks like it should perform that way. Finally, (maybe) the 2.3s have a lot of history on this site and a lot of wisdom for you to access. Mine has, knock, knock, never see a Triumph mechanic thanks to the combined wisdom of the old timers, for which I guess I am now one, on this site. The 2.5s are more of a mystery. We're still discussing different tires sizes, how to remove the tank, tunes, etc. Beyond that it's largely uncharted territory. I can say, having both, that either is a good choice. If you're into the twisties the 2.5 is probably the best choice. Into long cruises and the classic look (not to say they also don't do surprisingly well in the twisties, considering the extra weight) then the Roadster, Classic, or Touring model is your ride. Good luck with your decision....