Thank you everyone for the advice. It means a lot. Tomorrow it is supposed to be in the mid 50's after a few weeks of 20's and 30's here in NJ with snow and ice. I don't like to move plastic around in the freezing weather. I'll take advantage of the temps and straighten out that furler track and lay it next to the boat flat. Unfortunately its going to be raining to so not much else will be happening.
As for sails, I agree that new is probably the way to go. There is a reason why someone replaced their old ones and now selling them. So that will be a spring purchase. I am also debating on the 4.5hp outboard I have and may just pop for something newer. From sitting, the one I have is stuck. It isn't the first time I freed up a stuck outboard, I'm just looking ahead in case this one is too far to save. The deep cleaning will happen soon enough. Just waiting for the weather to break. I started a speadsheet of things to do, check, repair, clean, restore etc.
I'm sure once I actually start to get into the project I'll have a ton more questions.
Thank you all again for the input. I am also planning on videoing some of this project and sailing journey and posting it on YouTube. I did it with a semi truck project I purchased back in 2012 and a lot of people enjoyed following along. If/when I do, I'll post a link if allowed.
As for sails, I agree that new is probably the way to go. There is a reason why someone replaced their old ones and now selling them. So that will be a spring purchase. I am also debating on the 4.5hp outboard I have and may just pop for something newer. From sitting, the one I have is stuck. It isn't the first time I freed up a stuck outboard, I'm just looking ahead in case this one is too far to save. The deep cleaning will happen soon enough. Just waiting for the weather to break. I started a speadsheet of things to do, check, repair, clean, restore etc.
There is a sailing school near me and they have instructors who will come on your boat and teach you how to sail on your craft. I think this is the right move as not only do I learn sailing skills, but learn them on my own boat so there is no confusion. I also have a friend who grew up with a 27' Catalina who has already said he will come with his two boys and we'll make a day and show me what to do as well. As for the overwhelmed, a little truth, a little clickbait.What I did was to take an introductory sailing course over 4 weekends, and b. pay for an extra couple of private sessions with the instructor first to go over my boat and its equipment and then to spend a half day out on my first sail. By the end it all made sense, and for relatively little expenditure.
To the OP I would say: Get some help. If you have, or can make, a friend with experience of sailing, that will make all the difference.
I'm sure once I actually start to get into the project I'll have a ton more questions.
Having power boats all my life, I have always lived with the rule "have a doubt, throw it out". There is nothing worse than breaking down on the water and having to get towed back.The big difference is with the rigging, you could have some failures that you really don't want to have. If you see something and say to yourself "I'm not sure about this, it looks iffy." then it only becomes a matter of time before you say "****! I knew I should have replaced that!!! Yeah, TowBoat US?, this is....", so just fix early.
Thank you all again for the input. I am also planning on videoing some of this project and sailing journey and posting it on YouTube. I did it with a semi truck project I purchased back in 2012 and a lot of people enjoyed following along. If/when I do, I'll post a link if allowed.