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I haven't really had that problem here, with leagues changing affiliations and forcing a uniform change. The rec league I work in the summer is independent, in that they aren't affiliated with any particular sanctioning body. They run both baseball and softball and as long as the umpires match, they don't care what you wear. Most guys show up with every color under the sun hanging in the car, then pick one depending on the weather or what his partner has.
High school baseball and softball here have identical uniforms, so one set works for both.
I did have a buddy beg me to work a few of his NSA tournaments the past few years. I had to pay to register with them, plus buy a shirt and hat. The first tourney I worked five games and netted about 25 bucks! But I've worked a couple more for him, so the new uniform paid off. And, of course, this was by choice, not something forced on me by some organization.
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