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No transmission problems to date, and I pray to god none in the future. I don't know about the 36"-37" tire range, but I will say you will just have to take it easy. Part of the running bigger tires is learning to deal with going a little easier on your truck on the road. As long as you can live with that the KM145 should hold up ok out in FL. Same size tires in the mountains out here in NC.... I would say no.
Yeah I hope it will hold up! How bad is the steering with 34s?

'88 Raider, 33" Maxxis, 2" body lift, 10K winch