Looks like you are having a great time with new Cal 22. My guess is after a few times in and out of the marina/slip, you will be comfortable maneuvering....we all go through that to some extent.
I suspect my Cal 22 probably has a different reef system than yours, so I won't try to guess at what yours might look like....I can't figure what you lubricated, and to be honest I have never heard of a messenger line.
My reef line starts in a cam cleat, cabin top starboard, right next to the main halyard. It runs to the mast base, through a block, up the mast. Then I ran it through my cunningham loop, back down to a block forward on the boom, all the way back to a block on the boom aft, up to the last reef point on the leech, through that and down the other side of the sail where it is tied off on a small cleat. I'm sure there is a pad eye or two in there somewhere. So mine doubles as a cunningham/downhaul too. I believe this is a Jiffy reefing system. It works great for a single handed sailor. I can take her up into the wind and have her reefed in about 30 seconds.
And by the way, if you haven't noticed yet, Cal 22 sail much better in a blow with the main reefed as opposed to only reefing the genny. You get much better control of the boat with the main reefed and as much genny out as you can handle.
The slugs deteriorate in the sun and break after a while...buy a bunch and keep them handy.
I used to have anxiety about motoring into the slip too....now I sail in.