I made the jump from a 19k mile 2002 Sporty (nicely modded, and QUICK!) to a '94 Heritage with 47k miles back in March. I think your ultimate happiness will depend on you being honest with yourself about what kind of riding you do. For me, most of my miles are done commuting to work and back, with occasional fun rides with friends (typically 60 miles or less), with a few longer 200-300 mile days strewn about over the season. I bought a pillow top touring style seat for the Sporty which made the long days in the saddle much more palatable, and wouldn't have given it up but for a series of circumstances (accident in March) which led me to sell it to a buddy, and use the insurance money to buy my Heritage. I'll be honest... Until I had an opportunity to get on the Heritage and just ride out a couple tanks of gas with no particular place to go, I was kinda regretting the decision. My Heritage is NOTHING like my Sporty was. Comparing them back to back, the Softail feels like a dump truck. It feels ponderous and doesn't do anything quickly. The Softail feels heavy in the turns, slow to accelerate, and even slower to stop. Once I stopped trying to ride the Heritage like I rode my Sportster though. things started looking up. You have to be honest with yourself though... If you're looking at buying a bike for that one ride per year that you're going to do a 300 mile day that you can't do comfortably on the Sportster, you may be disappointed. It'll be great
that day, but how/where/when are you going to ride it all the other days?
Like I said, be honest with yourself. Look at the riding you do, then look at the riding you want to do. Once you're decided on what kind of riding you
want to do, it's time to look at whether you're in a position to pursue it. For example: I
want to load up a bike and take a 3 week trip across the country. However, I have a job and a family at home, and it isn't really feasable to do that right now. When I'm in a position to do it, I'll buy a Road Glide Ultra. In the meantime, I don't want to haul that much bike around in my day to day riding, so my Heritage suits me just fine.
Don't take this the wrong way, I'm not discouraging the purchase of an EVO Road King. Not by any stretch! I no longer regret the purchase of my Softail. I do regret letting my Sportster go though... So much so, that I'm looking forward to buynig and building another Sporty to park in the garage alongside the Softail some day.