I have a few orders that I can't ship because it says the period of eligibility for purchasing labels has passed. Is there a way to fix this?
How long ago did they order the item(s)?
75 days ago
Oh wow. Ok...
I agree with @UppNorthEh that you should buy off of Etsy and then upload the tracking numbers if you aren't using Pirate Ship or another site that syncs back.
Your processing time on the listings I looked at are 2-4 weeks, which isn't 75 days, so I honestly would re-look at all of that. I don't think Etsy is going to take kindly to you taking that long to ship orders, even if they are custom made...
If you are in the US get postage directly from the USPS or a third party like Pirateship.
I won't even ask how long your processing times are.
I'm not sure why you can't purchase a label after 75 days, unless it changed. Shipped orders used to show the ability to purchase more labels - up to 4 per order - for 3 months. Can't check now, I'm on my phone.
In any case, Pirateship offers similar discounts as Etsy, and is very reliable and easy to use.