where thats a nice hunk of money, if you like the truck, and everything else is up to date on maint, even a good used car would cost more, and then you dont know whats been done to it over its life.
ive have a new tranny or two installed over the years. its nice when you get a good rebuild.
for that money, make sure they are going to change all the clutches and seals and any other common wear items. ask them if they can install a shift kit too. that will make it shift firmer and in the end make it last longer.
sadly many shops will find whats causing the issue then replace just those parts, leaving the rest of the re build kit on the shelf. ( you know to use its left over parts in other cars) so you get a repaired tranny, not fully rebuilt.
say it was slipping in first gear, they install new first gear clutches and reinstall all the old crap. aka repaired, not rebuilt.