Figuring out a good habit with regard to ordering new reeds can really help ease the uncertainty that comes from the changing nature of oboe reeds. Reeds typically go through stages from the break-in process to the point that they are used up. New reeds are often a bit stiff and uncomfortable. As they are soaked and played more often, they will begin to soften up and become easier to use. The most helpful plan is to always have reeds in various stages so that there are some ready/easy to play and some that are breaking in to be ready to play when the others begin to age out. How long this process takes really depends on the reeds, the player, and how often they are being used. I recommend ordering new reeds when the current reeds are in their most comfortable stage. This way new reeds can be received and begin the break in process while the other reeds continue to be usable. This will keep you from going through such extremes from old reeds directly to new reeds, which can feel very uncomfortable for the embouchure. Reeds will also typically last longer if you have more than one and can rotate them, rather than playing that one favorite reed exclusively. Learning this personal rhythm with your reeds can really help in planning ahead for important performances so you are not feeling a sense of urgency with getting new reeds and trying to break them in. I hope this helps give you some ideas to implement a reed maintenance plan that works for you!