A shoe cobbler should be able to replace snaps. Also, there are many videos on yt on replacing snaps in leather. The press and snap tool is not inexpensive but that depends on perspective. Wire baskets top mounted may break too btw and considering the type of riding you do it would likely be a matter of when. A porteur rack with a fence sounds like something that would work for you in that you can strap your bag and even more !
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