I'd look for an '02 if you are looking at 88" 5 speed bikes.
Last year for the forged steel crank and Timken tapered roller bearing main.
First year for the bigger rear axle,also has the 4 pot brake upgrade and sealed wheel bearing upgrade that the '00 & '01 models got which the '99 hasn't got.
Have geardrive cams installed and you've got a pretty bullet proof bike.
Some have carbs and some EFI,I like the carb myself due to it's simple reliable design,my 2000 has 160,000 miles on the clock now and I'll not have a worry about a fuel pump failure or electrical issue with EFI ever.

I also prefer cast wheels,never have to be trued and no tubes to deal with so you can use a tire plug in an emergency.