so I’ve now had this bike (2013 865cc T100) a little over 3 years. I’m still in two minds. The raucous Dunstall exhausts are long gone, but the AIS pipework is still in a box under the workbench. The original seat has been replaced by a Triumph K&Q Seat, which is a great improvement. The touring windscreen is a definite success. However... it still has the occasional throttle snatch at low speeds. There is a definite “tingle” in the right side grip, around 65mph. The steering still twitches when crossing lane divider markings. The early-90s Sportster it was intended to replace, is still in occasional use. I’ve upgraded a couple of its long-standing niggles, such as a decent seat and 2:1 Supertrapp exhaust. Some (used) Hagons are on the bench, waiting to be fitted. The Triumph definitely has more power, is generally smoother and more reliable - it doesn’t have the well-known Sportster habit of shaking things loose. It has a better transmission - finding neutral on Sportsters can be a challenge! It doesn’t cook your thighs in summer traffic. But, somehow, the black and orange brute hangs in there... I really don’t know.
It sounds like you enjoy them both for each different personality trait they have. Nothing wrong with that.