FWIW I would recommend building up your own confidence in doing the work yourself. Learning is fun but start with a trivial fix and build up from there. Don’t be afraid for it to get a bit tatty, as long as the paint is ‘functioning’ don’t stress and get depressed about it not being in showroom condition.
When I eventually got around to repainting Marys top sides the white paint was powdery with many micro-cracks. But she was solid underneath. I am guilty of putting good paint over bad and it is not a long term solution, the moisture can seep in along the seam of old paint.
But you do need to keep an eye on rot and it is good to have a friendly shop with whom you can exchange cash for confidence in a job done well. But I encourage you to wear you patches with pride 🙂
Personally I am a fan of having a good cover or shed and keeping fresh water off the decks when stored. IIRC Colchide is a good starting point so you should have many years to build your capabilities.