Has anyone had experience in producing their own labels on commercial
products, such as Avery labels. I can find lots of templates and
software to make the design and printing easy. What I'm most interested
in is how difficult they are to remove.

Currently I use the software mentioned but print on plain paper and use
a little bit of brushed on milk to adhere them. Not particularly
impressive to look at but functional enough to identify the wine and
super easy to remove.