After talking with a wise lady who is also a traveling singer-songwriter/mom, I decided to get an entire second set of makeup to use when we travel. She also recommended having designated travel clothes and a "performance outfit," for every new season, but I haven't gotten around to that. I'm not sure if I'd be disciplined enough to save a whole set of clothes exclusively for travel AND to have to wear the same outfit on stage for a whole season. I think I would long for some variety. It DID, however, make me realize that when I go shopping I should keep an eye out for clothes to wear on stage.
Anyhow... buying a whole second set of makeup was quite an expensive undertaking, but SO worth it because of the amount of traveling we do. I went to a M.A.C counter at a department store and asked to have my makeup done. Looking back, I wish I would've waited and gone to an actual M.A.C store, because the girl who did my makeup was not as experienced/professional as I was hoping. It was still really fun to get some girl time.
Here's my attempt at a self-portrait of her handiwork. This is the evening look (and don't worry about the little brown spot in my eye... the doctor says it's just like a birthmark):
... and up close: