If you're going to be doing longer rides, as well as around town, I really don't think you can beat one of Harley's touring bikes, either a Road King or an Electra Glide. I got back into riding (after a 3 decade long layoff) in 2002/2003, and bought a Honda A.C.E. Great bike, still have it; however, I bought a new H-D Electra Glide on Valentine's day, 2006. I kept the Honda, figuring I would use it around town, but use the Harley on longer trips, since the H-D was so much heavier (800 lbs vs. 500 lbs). Haha! Over the next three years, I rode the Honda twice (or, maybe, three times). Once adapted to the Harley and used to its weight (took all of 2 or 3 hours), it is not only superior on the highway, but it would out-handle the metric bike in town and at low speeds, just no comparison. I still like the Honda, still have it (paid for is the best option), and I am back to riding it after a guy in a Cadillac SUV decided he needed my lane more than I did while I was on the Harley. Oh well, at least I got it slowed down enough before I went down that I'm still around (touring bikes don't make very good dirt bikes), but the scoot was totalled. I plan on getting another one sometime in the near future, 800 mile days were easy on that bike, actually felt refreshed after such a ride - I don't even want to think about riding that far on the Honda, even though I replaced the stock torture rack (saddle) with a Mustang seat and made other mods, many of which involve comfort. Heck, riding 300 miles in one day is a pretty long ride on that bike, and you feel it at the end of the day. With a stock seat on the Honda, 50 miles can be a torture test for your body (that applies to most metric bikes, BTW). One other thing - the newer H-Ds are notably superior in quality (unlike the bad old days of AMF ownership). Excellent fit and finish, you don't find chrome plated plastic parts (H-D still believes in metal, unlike the chrome plated plastic found all over most metric bikes, such as turn signals, mounts, etc.), and the air suspension on the touring bikes is a delight to ride. The fuel injection keeps that V-Twin ticking whether you're at sea level or 8,500 feet, too. I usually averaged 45-50 MPG on the Harley, pretty good for a big, heavy bike. Oh yeah, it doesn't seem to get blown around by other traffic anywhere near as much as a lighter bike, and it actually makes you want to hit the highway, as opposed to the "I really don't want to be here" feeling you get on a lighter bike out on the highway - the Honda is very "buzzy" at highway speeds, and the suspension just doesn't give you a warm and fuzzy feeling, completely opposite with the H-D. Don't get me wrong, I love my little Honda, but it just doesn't stack up to an E-Glide in any way. Oh yeah, the maintenance - mine never needed anything beyond standard maintenance (oil changes, etc.), never broke down, not even a hiccup (definitely different from the dark days of AMF). It is really a modern machine which looks a bit old-timey. If you get an E-Glide or a Road King, I'm betting your 300 mile trips will soon be extended far beyond that, all the time with a smile on your face!