What things have gone wrong with the motorcycle?
I should mention that I bought two, brand new, out of the box, XL883s at the same time. One for me, one for my wife.
OK, well at 750 miles it left me stranded on the side of the road, at night, in the dark. As it turned out the ignition module fried and I had to call my wife to bring the truck. Due to my unfortunate circumstances, I had to buy the module from a non-harley repair shop and install it myself. Such is life I guess.
At about 2000 miles my bike developed an oil leak from somewhere under the engine. It wasn't much of a leak, but enough to leave little tracks in the garage floor. I never got that fixed.
The screws that held the side cover that covers the electronics opposite of the battery, all decided to fall out one by one. This happened on both of our bikes. I had to end up using some RTV sealant on the threads after a couple of sets of screws were MIA.
On my wife's bike, the valve cover gaskets all of a sudden began to leak like nobody's business after about two years. Instead of taking the bike to the dealership, I just bought some gaskets myself and replaced everything from that point up. It was an easy job and saved me the downtime.
After about a thousand miles, I had my 883 converted to a 1200. That was the best money I ever spent on the bike and avoided the apparently inevitable leaking valve cover gasket incident. I had the custom so the handling was OK, but not great. My wife had the hugger and it probably handled better, but, lacked ground clearance for serious canyon carving.
I found the Harley seats to be some of the best factory seats I had ever sat on. The Sportsters do vibrate. Holy cow do they vibrate. On the custom I found it to be virtually intolerable on the highway as the vibration through the drag bars was a major issue. However, for tall people the forward pegs and the drag bars feel great.
We put the Harley forward controls on the hugger. That made the bike a great little ride and for all day riding a better bike than the custom.
All things considered, if you want an around town bike that cost a little more to own than a bike from Asia, get a sporty. It is fun as heck for short trips. However, if you're looking for a bike that will be reliable and comfortable enough for some highway trips, don't even consider the pre 2005 XLs.