What exactly do you want to know? I own a hot rodded 93 formerly 883 now a 1250. As such I am intimatey familiar with this era of sportsters.
90+ are all 5 spd
93+ are all belt driven
93-95 are the lightest bikes
95+ the speedos are electronic and no longer cable driven
2000-2003 have the best brakes and have sealed bearings in the wheels
in this era of sportster you are beat of buying a 883 and convert it to a 1250, often cheaper this way than getting a 1200 from the start. The biggest advantage is the 883 heads can be machined to get you up to 105HP/90TQ, after that you need a set of buell heads or 2004+ 1200 heads. If you want to be cheaper a 883 can be bored out to 1212, still getting you almost double the stock power of a 1200
Stock suspension blows, luckily a front sprig set from progressive is cheap and fixes it. For rears a lot use street glide or road king shocks as they are cheap and a good upgrade. Lots of options out there to fix this
Stock seats suck donkey balls, get an aftermarket
Stock brakes pre 2000 are crap, easiest solution is to swap on a set of 2000+ 39mm for sliders and use sportster, vrod, or touring calipers from 2000+ bikes.
Tanks have small capacities as you'll only get about 80-90 mi on the stock peanut tank. Lots of options out there to get bigger tanks
If the handlebar bushings are worn it vibrates a lot more, it's a wear often that is often overlooked. OEM rubber give the most dampening, but wear the fastest. Poly last longer but are stiffer, and metal will vibrate the most and never need to be replaced.
The engines are tanks, it's gonna last a good long while, worst case they are easy to rebuild yourself. Don't lug it, they like being above 2500 RPMS and lugging will damage the crank. Just be aware they are hot engines. Mine sits around 220-250 degrees when running. Keeps your butt warm.
Choke cables will snap off if you over tighten them, finger tight plus a 1/4 turn with a wrench
Oil tanks in 93 and prior like to crack at the mounting points. 94-?? Are better and I think 2000-2003 had it sorted out.
If the bike does while riding it, but restarts after sitting for a bit your nose one IGN is shot. Replace with an aftermarket unit since the OEM Is crap and an obsolete part
If you over tighten the clutch cable on the primary case you will crack the nut and it will leak oil down the cable. It's possible for this to loosen up and weep oil too, a quick snugging might compress the o ring enough to stop it. On pre 94 bikes you have to take the cover off to replace a clutch cable, after 93 you get a bigger primary derby cover which makes it a lot easier and IMO looks better
If I were wanting an easier bike to mod stick with 95-2003, mostly looking between 2000-2003 for the better brakes but that can be fixed relatively easily and cheaply with ebay parts if you want. Main reason is parts availability is better for these years and you get an electronic speedo.