First thing the commercial tower crews do:
Use courtesy tape. Just the usual 3M verity put a wrap around the connector nice and even then they use stuff they called Mastic, one layer then another layer of vinyl tape forming a seal.
I have recently put the courtesy tape and sprayed flex seal to test it, Only been in the air a month and still RF wise checks good. I'll take the antenna down this fall when weather cools off and open it up to see the result.
The courtesy tape is called that as all you need is a sharp raiser knife and make one slice and the tape takes off the Mastic and the flex seal in one operation. If you get too much mastic goop and it oozes out. just leave it alone until you have to take the connection apart. Then clean it off using Zippo lighter fluid. Just a little dissolves the goop mastic.
They also use this connector seal made by Andrews corp. that has a spiral pull inside the tube when the spiral plastic is pulled out the tube shrinks rapidly. Nice stuff and easy to remove but for me it is expensive. No heat needed.
Another trick I have seen them use is wrap the tape on a screw driver back ward (sticky side out) then start the tape on the connector and unwrap using the screw driver to unwind the tape. Takes a little practice.