Here's a pretty good youtube channel.
https://www.youtube.com/channel/UChqnU1FRDDGNkf18sWpC8YgThe guy is owns a baseball shop in japan and most of the vids have english subs that make sense most of the time. He shows a lot of vids of fixing old gloves for you guys that like to do that kinda thing and sometimes shows some really sweet custom ordered gloves by his customers and he breaks them in.
Once my glove gets sloppy and the pocket isn't to where I like it, I give it away. Usually my outfield gloves last 3 years playing spring, summer, and fall ball and my current IF glove is going on 7 or 8 years now since I play 2nd or 3rd maybe twice a season.
I'm still deciding which OF glove I want. It's down to zett, asics, ssk, and mizuno and if I order a custom glove from japan, it'll probably be ready by fall season.