Pros: Handling, reliability, vibe.
Cons: Tempts me to skip work.
I ordered my 2000 Sportster XLH 1200 in December, 1999, from a dealer in western Wisconsin. All Harley models were backordered at the time, and it was common to pay hundreds of dollars, even thousands, over Manufacturer's Suggested Retail Price (MSRP). I was lucky to pay list and wait only 4-1/2 months. Seven years later you can walk into any Harley dealer and ride away with a new Sportster the same day. They may even through in some free accessories.
I had the dealer install Screaming Eagle II slip-on mufflers, rejet the carb and install a Screaming Eagle air cleaner kit before I picked it up. This "Harley Tax" gives you a significant horsepower boost and makes the bike slightly louder than stock. Later additions included HD saddlebags, a medium-height sissybar and rigid sideplates.
I've been thrilled with my Sportster from the day I got it. It was my first new Harley, although I'd been riding for nearly 40 years, and it's a great commuting bike. It handles well, gets decent gas mileage, has plenty of power, good braking and it's a blast to ride. My commute is mostly on city streets, and the Sportster is quicker and a bit more nimble than a larger cruiser. It's also great for more aggressive riding on twisty country roads. While Sportsters aren't considered long distance touring bikes, I've riden mine from Wisconsin through Minnesota, South Dakota, Wyoming, Utah, Colorado, Kansas, Nebraska, Missouri and Iowa. A 600 mile day is a l-o-n-g day on a Sportster, but it's not impossible. The vibe more than compensates for the vibration. The only situation where it doesn't shine is in heavy interstate traffic, and even there YMMV.
The Sportster is the most reliable bike I've owned, including various Hondas and Yamahas as well as a bunch of British and other European bikes. It's required very little maintenance and it's easy to work on. Aside from recommended dealer maintenance at 5000 mile intervals, it's been in the shop three times. Those were a transmission repair (shift lever return spring) under warranty, tire and brake pad replacements at 9000 and 18000 miles. In addition to regular oil and filter changes I've replaced the rocker box gaskets and the battery ground strap. I consider all of that to be extremely minor in comparison with previous bikes.
Six years later I bought a new HD Dynaglide (FXDBi). I really love the Dyna and I put a lot of miles on it this year. But I'm keeping my Sporty too!