None of the years are perfect - but when I do go out and upgrade (just spent the past couple of years saving like a mad man to refi on the new house and cut my mortgage in half, then got 4% intrest rate yayyyy! )
- there are only going to be 3 options I'll be looking at and in the following order, (understand you might not see it the same way I do.) I really, really like doing all my own work in the garage and grew up on carbs, going to a dealer for service work for "anything" is just something I can't stomach easily... for my Jeeps - they are obdII and I'll work on that all day long with a standard scanner vs HD's proprietary bullshit.
97/98 e glide - last of the Evo's - rock solid and all the kinks worked out, must have a carb, the FI of this era blows donkey balls, if I can't find one with a carb, I'll convert it.
2002 e glide - for all the reasons mentioned previously - again , must have carb, if not it gets converted and a set of gear driven cams is also a mandatory upgrade.
07 e glide - 96" and 6 speed, real throttle cables to a TBI - lots of other little issues - but better cam chain set up that the 88" and not as much of a need to change to geared cams (runout on crank would probably make it not easily work anyway).
best of luck to you and I hope find a bike that makes you happy !