Pre 2000 (1999) will be a 1340 EVO - 1999/2000 was the year the 1450 Twin Cam was realised.. it was a hybrid few years with both models having Carbs Or FI - the early FI units are to avoided as they will fail and you will need a carb conversion.
I’m an EVO fan, simple, easy to maintain - but the newest one is now 18 years old.
The evo engine is pretty bomb proof, but must be warmed up properly - the early TC model needs a cam chain tensioner upgrade as they break up - as mentioned the early FI units can cause problems - carb conversion is easy enough.
You would have to wait until 2009 to get the frame updates - so just a few engine changes between 1999/2009 ( 1450/1550/1690)
I use my evo all year round, ride it to Spain most years... but it does need a little fettling each year - but this more due to its 106,0000 mile history!!!
With Harley it’s as much about budget/Model - so much choice - Touring, Softail, Dyna - what do you want?
Tour? - Tinker? - Ride hard?