I read with amusement your 4 year struggle with a Sportster. I've got a 2000 Sport model and have had a few of the same problems. But overall, while the Sportster isn't as reliable as a new Honda, it IS as reliable as a 1970s Honda, which isn't too bad. Harley sells a lot of Sportsters because it says Harley-Davidson on the tank. What most purchasers don't realize is that the Sportster was introduced in 1957 and remains today a 47 year old design. For those of us who rode motorcycles 40 years ago, we think it's pretty cool we can buy a brand new 50-year-old motorcycle. But we don't pretend to believe a 50-year-old design can compare with a new Honda. Most of the 45,000 people who buy Sportsters each year should probably buy a Honda instead. But a Honda doesn't "turns heads on the street and in parking lot," doesn't have "the trademark vibrating rumbling Harley roar," or any of the other reasons you bought your Sportster in the first place. The Sportster is what it is. It's a 50-year-old design. Your sticky gear shifter is a manufacturing defect, not a chronic problem. Harley should've fixed it. But many of your problems were partly self-inflicted:

1. The oil leaks. The rocker cover leaks are a well-known problem. The new metal gaskets introduced in 2002 solved the problem. As for the leaky head gasket, you admit to overheating the motor in a "particularly hot ride in slow, heavy traffic on the freeway." Remember in 1957 there were no freeways and not much traffic. I lost both head gaskets when I got stopped for an hour in D.C. traffic at 105 degree. Replaced the entire top end gasket set over a weekend. Haven't seen a drop since.
2. The electrical failures due to corrosion. You store the bike outdoors? Sorry, but storing any bike outdoors, including a Honda, will destroy it in a year or two.
3. Parts falling off. Buy a tube of blue Locktite. And a torque wrench. It's a 50-year-old design.
4. Detonation? (Or as you call it "dieseling.") I'm guessing you never fixed the EPA jetting. Remember there was no EPA in 1957, and it's hard to get that old engine to pass modern emission rules. The solution is to screw the EPA and turn the pilot jet out a full turn. That will cure the detonation.
5. Now, what you called the "final straw." You've been complaining about fuel starvation at highway speeds for 4 years. And then the petcock stops working. Bingo! Can't blame that one on Harley. The petcock is one of the many Japanese components on a Sportster. You said at the beginning that you "place much greater weight on engineering than aesthetics when it comes to bikes." And you bought a Sportster? Sorry, it is what it is -- a 50-year-old design.

Respectively yours,
John Spofford
(Old fart on a Sportster)

PS: I've had no dealer problems because I won't let those idiots work on my bike. As for my Hondas, they never need any work ;-)