Salty Jack:
I've offered you my opinion on engine (outboard) shaft length in your other thread. I can't recommend sail makers from experience but, I can tell you that I've ordered a new main with two reef points and 75% jib to match the conditions I expect with my new to me 1988 C-22 which will be berthed in Oklahoma. Oklahoma is one of those states where the winds blow often and, they can and do blow hard. Very hard steady, and the gusts pack a huge punch. Just this past weekend there were reports of sailboats capsized and some boats de-masted on Grand Lake, OK. There were no fatalities thank God. The weather was forecast to turn but until it did, it was a beautiful sailing day. It was no surprise to me as the front passed through and social media showed fishermen hunkered down under bridges with 2" sized hail on their boats. What I was doing on this fine sailing day was finishing up my re-rigging project on my new to me 1988 wing keel C-22. While I think that new sails should be on your radar (as they were on mine), unless you have provenance that the boat has new rigging that this be your priority. In my case - and I have no complaints, no issues and absolutely no problems with the PO and, he will be the first person that I invite to go for a sail with me - I ordered new standing rigging and replaced it this weekend while boats were being knocked down approximately 70 miles +/- away from me. What I did find, while doing the refit is that all the stays and shrouds looked great at first glance. The back stay was replaced once previously but looked sound. All other rigging looked in good shape until I went to replace the starboard rear lower shroud. That shroud had two broken wire strands where they passed over the upper thimble and the main halyard was frayed as the thimble was being deformed under the load while sailing. This only became apparent when I removed the shroud. Moral of the story? On older boats like ours, it is imperative to set priorities and rigging in my opinion, is one of those things that isn't readily apparent with a quick inspection or even the recommended "cotton glove" treatment. Unless the PO can state the rigging has just been replaced and you can confirm that, rigging needs to be close to the top of the list when improving your new boat. Sails, engines, leaks, spiderwebs etc. are all important but a sound hull and rigging are the foundation for making sure we are ready to sailing.
Now, to your rudder questions. Keep your rudder as is. It will work for now but plan to replace your rudder with a Rudder Craft Kick-Up Rudder. Last year they had a long wait and if that's the case this year, you might consider discussing with them how long the wait is expected to be this year. In my opinion, Priority One - Hull soundness. Priority Two - Rigging. Priority Three - Toss up - engine, sails or rudder.