tmieyal,
Is this coupler the official Davis one, or some "telephone" coupler? If it is the latter, it is no wonder you are having problems with water infiltration. I submit that you will never be able to keep water out of this type of coupler outdoors.
Davis used to sell the coupler (7960) separately, but I believe that it is now part of an extension kit. (I could be wrong, but Davis and the "usual suspects" suppliers do not list the the 7960). It appears that you need to buy an extension like the 7876-008. (e.g.from
Scaled Instruments)
This waterproof coupler, has a sealed compartment and the actual connections are made with gel-filled crimp connectors. The RJ connectors are cut off and the wire ends are crimped into these gel-filled IDC crimps.
I have used this coupler in the past for extending my solar sensor, and I never had any problem with it.
By the way, I drilled a new hole to pass the rain cable from the tipping spoon assembly and I got it to (just) reach. I drilled the hole opposite of where the heater is.
I think if you redo the connection with the waterproof coupler you will be fine. You could get the shortest extension and cut it to length. Unfortunately, this means cutting the existing Rain connector off. I had to crimp a new RJ connector when I moved and could mount the solar sensor back on the ISS.
I hope that this helps.
Greg H.