My suggestion to buy a 05 & up is strictly my opinion based on information and experience. Can you get by with an older Lt? Certainly. As for me I am spoiled with the extra horsepower, lower center of gravity, and the electric hydraulic center stand. The centerstand is by far the safest and neatest refinement. In the end a person should simply test ride a pre 05 and compare it to an older one. Unless one is hampered by budget constraints the choice will be obvious. However, an earlier model Lt is better than no LT. There is only one problem with the LT's. Àfter you ride one it ruins you for any other bike. At least out did for me.
As I have said before, test ride both and early and a late. I did and I fell in love with my 2000. For me the servo brakes are over powered and I like the feel of the 99-01. I prefer the early dash, the late one seems too busy and hard to read at a glance. I also like the black coloring as apposed to the silver around the dash.
As for riding it, the seat position is slightly different. I do not want the power center stand, extra stuff to break. I am 45, 6 ft tall and 195lbs. I am in good shape and don't need the assist.
One more thing, I have a base model 2000, no chrome, no bike computer, no 6 disk player and I love it that way, everything I want, nothing I don't need.
With all this said, ALL LT's are great bikes, ALL are going to be great to ride, ALL are going to make you think there is no other bike on earth that can compare.
You need to ride several, different years, find out what you want, need and don't want. I spent almost 6 months from deciding to get a new bike till I dropped money on my LT. I rode about 15 bikes and could not find anything I liked better than the LT. My first LT ride was an 03.
So, ride many, and have fun. See you on the road soon