I've only had a 1976 XS360 Yamaha (my first transportation at 16), a late 80's Honda V45 Sabre (that bike was kind of a pig) and a 2002 750 Magna before my 2016 DSR. Since the DSR is the only one left, I have to put it at #1! I don't regret my purchase at all. It's been a great summer. I just reached 3500 miles on the odometer last weekend (purchased in April this year). No commuting, but lots of night and weekend cruises. Zero problems with the bike so far, other than getting tossed off of it in the driveway due to my lack of respect for the rear wheel torque on wet pavement (and it was undamaged, and I was lightly damaged).
Since I can't ride the bikes side by side, it's hard to recall experiences, but I can say the DSR's effortless acceleration always brings a smile to my face. The only downside is that due to it's relative light weight, it feels a bit squirrely on the highway above 60 compared to the 2002 Honda, but I also did not get to run the 2002 Honda through the woods like I do the DSR! I am sure a decent wind screen could help there.
Steve