Pretty generic question. How much money are you willing to spend, how mechanically inclined are you ? Many modifications. From lightening to engine mods and component upgrades. My brother and I have many hours and money invested in our 88 which I would say is probably a div. 2 tractor. We never had to meet ntpa rules here just the club we were pulling with. So to be totally honest I do not know what div. 2 rules are. We did 90 percent of the work ourselves. Might want to try the pulling forum here.
 
Just hook it to the sled. Even an original stock 88 can still be a pulling tractor. Not a hot rod version but still a pulling tractor, and I suspect just as much fun to own and pull with as those that spend the family fortune to win a little plastic trophy or a ribbon and some walkin' around money (the money in some places).
 
Sometime you can win more than a plastic trophy-Son won this a Tulsa last Jan. on a Oliver 88.---Tee
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Well Tee, I did say some walkin' around money (in some places). Looks like your son was in one of those places.
 
A lot depends on the pull the the rules. I pulled with my S88 a few years back and ran 1st and should have run 2nd or 3rd and lost by 6 inches. I came in 4th place and the guy who won 1st told me after the pull he sure was glad I was 150 lbs light and ran 1st instead of 3rd. He told me if I had run with he extra 15olbs and in 3rd I would have left him way behind
 

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