HB! - Congrats on the "new" boat! Many years ago I owned a Catalina 27 that I kept at Spring Cove Marina in Solomons. It was the first real "yacht" that I had owned (my previous boats were dinghies and Hobie Cats) so I had lots of questions. I remember the first winter I hauled the boat at Spring Cove - Max, whom I'd met on one of the Catalina forums (probably Sailnet, which, at the time, was as popular as SA is now), met me one day on my boat. Because I live almost two hours from Solomons, I had a long list that I wanted to get through. All I can remember of that day was Max talking up a storm while I tried to work. I eventually just gave up and sat down to listen to him (I think was working on replacing my standing rigging and the spreader compression tube on the mast). It was the first time that I'd met Max and I ended up seeing him in subsequent years at the Annapolis Sailboat show manning the Catalina Owners booth. The last time I saw him was at Screwpile this year where we raced in the same class. We came close to trading paint a few times but it was funny during one mark rounding when we rounded with our bow 2 feet from his transom when he yelled back " are you guys still there? Geez, I can't get rid of you!!". Good times. I know you know Max but bottom line is he has a WEALTH of Catalina 30 knowledge and I would take advantage of him every chance you get. He may even be able to help you prioritize your list.
If you want to get a decent set of Catalina OEM-like sails that are good quality and will hold up, I recommend ordering them from Rolly Tasker. I ordered a mainsail from them for my Catalina 27. It was a very nice sail.
Toss the cushions and have new ones made. I've been through this twice with boats I've owned -- you will never get the smell out of the cushions - ever! Toss 'em and have some new ones made. They ain't cheap but you may be able to order some from the factory.
I would definitely haul the boat for the winter and unstep the mast. Replace all the running rigging and, if I were you, replace the standing rigging, too. You can get very good, reasonably priced rigging from SECO South in Florida. They duplicated my rigging on two boats and did a great job. Just coil up and zip-tie the old rigging and ship it to them and they will duplicate. I would also consider replacing the lifelines, too. Doesn't cost much more and it will give you piece of mind. Go the uncoated route.
Good luck with the new boat. You're probably going to need another job!!! I teach engineering at a local university - the money I make is my boat slush fund.