#1
In order to replace the bridge single coil in a tele with a humbucker, does the body have to be rerouted to make space? Or will the humbucker fit in the current space?
#2
you could take your pickguard off to make sure next time you restring
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#3
I believe most Teles are not routed for a humbucker in the bridge position. Since the standard Telecaster bridge-plate is installed the way it is, it is a much bigger modification than just switching the pickguard on a Strat. You will need a new bridge too.

Because of that, the only real option is a Tele-style single coil-sized humbucker. Note that a Strat pickup won't find in the bridge position of a Tele, nor would it be possible to mount it with the screw holes in the bridge plate. Seymour Duncan makes a Little '59 for Tele that is quite good, as well as a Hotrail for Tele.

Some Teles are routed for a humbucker in the neck-position though, and for that you only need a new pickguard of course, but it is definitely not as common as Strats routed for HSS or HSH, which could be considered Standard on modern Strats.
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#4
Mexico and MIA Standard Teles will be routed to fit a humbucker in the neck position. You'll have to order a new pickguard, but otherwise it's a drop in replacement, plus the two solder points.
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#6
I always thought it be would cool to put a TV Jones in the bridge position of a Tele. I know there are versions that have a humbucker in the bridge position but seem to be few and far between.