There are two points to make, one on the re-cutting of sails.
One has a very good chance dealing with "good" old sails and "money saving", to end up with neither.
Additionally, to the extremely stressed relationship with one's sailmaker, after requiring him to do the impossible, one has a very good chance to end up with a rag, looking like Mother Hubbard's washing, and costing him almost the price of a new sail. Besides, the "new sail" is going to be an eyesore for the rest of the sail's life.
(A storm sail cut from a heavy, used main, is entirely different proposition.)
We are dealing with one every race, a no1, which is trying to do it's job but is failing every time because it is not made for the boat it is being used on. No word to the owner would get through, as usual, he would not consider any criticism from anyone

.
Ordering a new sail is the only way to get what one needs, hassle free. Measured, made, fitted by the same guy whom one can talk to! is the go. The cost, yes, is considerable but so is the satisfaction to have a good sail and keeping your dosh in the country where you live. I could not live with a ****ty looking sail on my yacht.
The nature of a second hand sail is to be w o r n . In a worn textile, like sails, the threads are pulled in different directions while in use, modifying the lay of the threads from the unstretched original material. Re cutting this stretched fabric is next to impossible. This is the reason, decent sailmakers are not too keen on re cutting old sails.
The second point is on the lazy jack and the reefing caper.
This seem to prove my point of not having a lazy jack on my boat. As long as the sun is shining in the breeze, no problems.
Problems only arise when the going gets tough.