Thanks all. Since fixing the tranny would cost about what the truck is worth (and also it has some other issues...), I'm hoping it's clutch related. I hadn't even thought about the pilot bearing and was trying to figure out how a sticky throw out bearing or loose pressure plate could do this. I'm liking the pilot bearing idea.
I think the mechanics around here mainly see automatics, and two reputable shops have told me it's the transmission synchronizers, but that didn't seem right to me.
A new clutch every 150k isn't totally unreasonable, especially having trained one teenager and a wife that didn't grow up driving a clutch.
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