I've been very surprised at how helpful performers are, & how much it means to them, to get positive feedback. Especially specific positive feedback, not just "I love everything you do",(which is always nice), - but what & why... And I've been surprised at how much their responses have meant to me. It's like completing the circle - I'm not just passively listening to a stranger, & they're not playing to a bunch of passive strangers.Email is a wonderful thing for fans & performers, and especially songwriters who don't perform & have limited contact with fans. Phone calls are a bit invasive, & snail mail is tedious & slow, but emails are JUST RIGHT! I tried to keep in touch with a couple of my favorite performers who I'd helped host when they were on tour, & now that we all have email, we do keep in touch now & then. But most of my contact with performers is just one time questions or one time praise - just perfect for email.
I've found when you ask about specific songs or techniques they're very likely to respond, because that's what they're doing this for - the love of the music. I wish folk performers made the kind of money they deserve. But since they don't, they really deserve being appreciated. Alot of them are people persons, & enjoy contact with fans. Some of them are incredibly insecure, no matter how great their musical talent. Folkies tend to be a very humble bunch, so you probably can't go overboard in expressing your praise, interest, or questions.
From my experience, I'd say you have a very good chance of getting response from a performer, unless they're incredibly busy, or are extremely well known. (Other than someone like Pete Seeger, who is both, but people contact is hugely important to him...)