Well, I picked up a "gently" used 2003 FHDL Dyna Low Ryder with 1,046 miles on it in 2005. She now has well over 106,000 miles, and the jugs and cases have NEVER been pulled or cracked.
First off, I'm on old "Shortster" lover. I like "fast and furious". Had a '72 iron head with right hand shift (award winning rat bike), a '80 XLH (added a kick start) and a 2000 XLH (along with a 1965 FLH that was down more than it was up). All my Sportsters (as well as the Pan) had their individual unique quirks and maintenance issues which usually required carrying 50 pounds of tools whenever going on a ride. But, back then, you could fix 'em on the side of the road. Anyway, I digress....
My '03 Dyna is nothing more than a Sportster on steroids. Same front end, basically the same frame, but with that Twincam 88 and a 5-speed. And in all fairness, she's no longer stock. Harley had issues with the '00-'05 cam chain guides and chains. Replaced with gear and solid lifters. Installed a S&S .510 cam, S&S Super E carb, hotter coil and larger plug wires, iridium plugs, extended forward shift (I'm 6 ft 4 in), mini-apes,and a few other "upgrades". And as with any (older) make or model, Oil changed every 2,000-2,500 miles with GOOD oil and filter, primary and tranny every 5k miles. She's starting to lose a little compression, but still within factory specs. She still can "(EDIT)" and I've smoked my fair share of rice burners with it. Now that I have a Geezer Glide (2011 FLHTCU) I'll pull the jugs and do a top-end this winter. May even go ahead and split the cases and do a bottom job. Looking forward to another 100,000 miles out of her then.
Sentinel, no matter what you get, just make sure you fit and the bike fits your riding style and habits, and has the room for "personalization". Harley has certainly got their head and a** wired together on the new lines they're putting out, and have for several years now, starting with the Twincam and everything forward. Truly wish you the best on your choice. And as long as you keep the sunny side up and the rubber side down, it don't make no matter what you're riding...
Semper