don't know about #1.

as to water in the bilge; I'd wondered about this myself. Finally found at least one answer. Don't know where you're located, but if you get snow, it'll get down inside the gap between the cockpit hatches and then freeze solid. Creates little dams which are out of the sunlight, so don't melt as fast as what's exposed to the sun. Get a rain, or a warm day which melts a bit of snow and the water overflows those little dams and into the bilge it eventually gets. I'm sure there are other ways, but I've seen that one in person.

Kinera,
I can help with Q#1. A number of years ago I wrote an article on replacing the outhaul wire, and at the same time upgrading the outhaul purchase from 2:1 to 5:1 inside the boom. I'm guessing it was about five years ago. I just checked on the website and it's not there, but I know for a fact that it was published in Mainsheet, so it would be in the Tech Notes CD. I included a parts list and a detailed description of the project. Hope this helps.

PS-It would help if you could update your "signature" to tell us a little about yourself and you boat. Click on the "User CP" link above, and follow the directions.

I have the same era Catalina. I just ordered 2 rolls of the butyl tape to rebed the deck hardware as directed in the excellent articles available in the forum. If the backing plates and nuts below deck are discolored with rust they are leaking. Even though they don't outright drip it is enough to cause condensation and wet core issues. The chain plates have been the biggest culprit on my boat. Life Caulk has worked well on these. There is also a sizable amount of runoff coming down the inside of the mast exiting through the weep holes at the mast base. I presume a little rain gets in around the masthead sheaves and also wicks in through the halyard runs. Not much to be done about that. Also check to see if your gaskets around the ports, hatches and windows have deteriorated. I am slowly replacing all of mine. Between all of the various through deck fittings seeping a little it adds up to a bilge full after a rain storm in my boat too.

On my outhaul I replaced the wire part with 3/16 Amsteel (dyneema/spectra whatever you want to call it single braid). It goes to a 2:1 cascade, also made from the same matierial, then to a 4:1 purchase with 1/4" Sta-set double braid. Works great.