with a 2nd gen SC your in luck. There are two ways of doing a "repair/maintanence"
You can change just the plastic coupler inside which gets rounded out overtime with a oil change kit from toyota. Comes with the plastic coupler and SC nose cone oil. $50~ if i remember correctly in the beginning of this year.
next if you want to replace the entire nose cone, which rebuilds/changes out the bearing in the nose as well as the coupler mentioned above as well as where the pulley sits which is where majority of leaks seem to happen. Toyota also sell this nose cone replacement kit for 2nd gen SCs only for about $260~ if i remember correctly.
let me see if i can find that link again. i cant remember it off the top of my head.
by the way both jobs are easy, and are do-able with the supercharger still mounted.
Although it would be MUCH easier with the SC off its really up to you. job time can be cut in half without having to dismount the charger, but also can go against time as well with trying to figure out and get everything properly aligned and torqued with the SC still one. It comes down to what you feel comfortable with.
EDIT: found the link
https://trdparts4u.toyotaofdallas.c...2&catalogname=TRD Performance&idCategory=2161
Prices are just as i remembered, if anything a little cheaper.
Dont forget to change the belt as well if need be.