1usavet, First off, Thank you for your service.
Now about the keel. I don't know what type of trailer you have but it is probably a bunk type for that size boat. The other type is a roller. Either way this is what I have done . Jack up the trailer and boat, install dunnage under the trailer and boat, repeat until the boat is high enough for the keel blade to be dropped out. I then slid a 10 foot 6x6 under the boat at the front and rear with angled wedges screwed into the 6x6. These prevent the boat from rocking side to side. The trailer can be lowered and rolled out from under the boat.
Drop the keel carefully as it can be very heavy. Using old pallets can help with the keel drop. Reverse to install the repaired keel.
There is a web site called "Catalina Direct.com" that has a picture breakdown of all the keel parts used on the Catalina 22. Your keel will have something simular. Replace any warn parts! If the keel blade hole is worn badly then it is easly repaired by boring out and installing a bushing.
There are other ways to support the boat. This is just what I had handy at the time. My boat was a 26 footer and weighed about #4,000.
I had16 inch tall by 14 to 16 wide blocks of fir firewood rounds, unsplit. I stacked these up along with scrap 2x4 and 2x6 pieces about 16 inch long for my dunnage.
Get back to this site if you need more help or catch me off line.
Ray