Serving in multiple affiliations is really no big deal IMO, I work Baseball, Fastpitch, and SP.
Sure I have a rainbow of shirt colors on the USSSA side but that adds many options for me and my partner(s) in baseball and fastpitch that I welcome (Navy, Red, Black, Powder, Pink, Camo, Cream, and White). The SP side goes with Red or Black usually.
I can work one USSSA tournament and make my $400 and I cover the cost of all of my uniform needs for the entire season(s)...work a 2nd tourney and I have enough for all my gear as well. The rest of the season is gravy
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ASA is shrinking here in Michigan while USSSA is booming. However, it has been and will always be "the people" that make the organizations (leagues or tournaments) worthy of my services. I work very hard to maintain my credentials, training, and uniforms which allows me the ability to pick and choose who I work for and when I work as there is plenty of opportunity to do so, you just have to be true to yourself and diligent in your quest to work with those "people" that are deserving of you.