OP here, yes, it appears I'm overthinking it! I now asking for a specific stylist is a good thing, but I worry the stylist might be like "she comes in hardly ever, doesn't do much, she's wasting my time."
I'm a good customer otherwise - I think I tip ok for a simple cut/style, show up on time, don't cancel at the last minute, etc. I'm somewhat of a people pleaser though, can ya tell? lol.