I'm currently running an '06 XL1200R Sportster, this has the rubber mounted engine that was introduced about 2004 so I am reasonably isolated from the vibration. The 2000 model you mention will be a far harsher ride because of this. However if you are prepared to put up with said vibes the 1200 Sporty is a nice bike.
They are very easy and cheap to maintain and generally reliable, and parts are easily available. Nice torquey motor, pretty quick accelleration up to about 90mph, and the handling is pretty good considering. Many people including me usually fit the stage 1 tuning kit to free up an extra 7-10hp, makes a big difference (K+N air filter, rejet carb, free flow exhaust/silencers)
I usually use mine for fairly local stuff and use my GS for 2 up, and touring and long distance work. That said I covered best part of 1500 miles on the Sporty last summer touring northern Scotland over a few days. Averaged over 55mpg, and was well suited to the highland roads. Like BMWs I think Harleys are an aquired taste, this is my second HD since 1999, and I really like them.
They are not everyones cup of tea, and I've found the biggest critics of them are usually people who have never ridden one or only covered a few miles on them. Like the GS, be prepared to spend money on bits and pieces for it, it becomes addictive. Read the book 'Hog Fever' by Richard La Plante you'll see what I mean.