The FNG!

So I am pretty new to the ATV thing but I have been involved with powersports my whole life. I have a 2001 Sportsman 500HO and just picked up a 1993 Trailboss 250 4×4. The Trailboss needs a new top end and I am wondering if it is worth it to over bore it and if so where should I take the pieces in the metro area (Minneapolis/St. Paul) to have them machined. In addition what suggestions does anyone have in regards to carb adjustments / jetting for an over bore of say .020?

Thanks for the help ya’ll