As others pointed out, have slugs installed on the mainsail luff and keep the track lubricated with Sail lube or the equivalent. Older and light weight sails are easier than new or heavy cloth sails to handle. You probably don't have heavy weight sails on your boat. The self tending jib is a complication. Does it have a boom? Our staysail has a boom and mostly I like it. It all depends on how well it was rigged and how you use it. If you single hand in very close quarters then you will probably come to like it more than if you sail in more open waters. In a moderate sized sloop such as yours, I would probably not go for a self tending jib. But if it's set up well it may work great. We have long had the rule to not change a boat until we have used it a lot. Sometimes what at first seems like a better idea really isn't .