Killjoy,
By the time I started really mod'ing my 821, she was paid off and not worth enough for the upgrade I would want. And I didn't want to part with it, just wanted a bike for each activity, which I couldn't afford. I really do love this machine. Plus, while I'm pretty good at wrenching on cars, my bike skills were novice, at best. I've gotten into some really tight spots doing deep maintenance and this forum has rescued me every time. You can make it really fast and handle really good, but it is just not designed to travel highway slab for long distances at high speed. I have an assortment of windscreens and still get beat up on longer treks. While it handles urban environments well, she really doesn't like going slow (more of an early gen issue). This is where tuners, airflow, evap delete and gearing can help.
Mine was pretty good with front fork inserts and OEM rear, but I had some adjustment to play with in the rear. I'd list steering damper as must-do if you do a lot of highway miles above the speed limit. The front end gets very light and twitch above 85 mph. In this setting, which is daily on my commute, I dream of a Multi or BMW. But, honestly, if I'm gonna go big touring bike, I'm all in on a Goldwing.
I've got 23K miles and most of my serious issues stem from me trying to fix or mod something myself. Can't speak highly enough of the motor. I have beat the living snot out of it since break-in and she always reports for duty. I would not have purchase one of the older air-cooled modes. Not enough power (for me) and way too-short maintenance interval. The 821 ushered in a revolution for Ducati regarding durability and valve/cam maintenance, and it's only been getting better. Like, when the 1260 came out, I thought 'if that's just a bored out better version of this...sold'. I think they make some of the best motors on the market today and the V4 line is insane. Ditto for electronic rider aides, which thankfully started on the 821. Big fan of their DTS and ABS, even in early form.