It wouldn't make a difference to me at all. I might inquire as to why, but unless it's a disease, it wouldn't matter to me why. Just because he hasn't been with someone in a while, or at all - whether by choice or being rejected or just not having time - means nothing with regards to whether I'M attracted to him. I don't care what others thought - all that matters is what I think and feel and what he thinks/feels.
Bring it on!
As for the very experienced... I do feel a little more negatively about them. The less or medium experienced, I've found, are more honest in their reactions, more passionate. If you've been with 30 women, I'm guessing you don't take sex very seriously. I like a good roll in the hay like anyone else, but being one of dozens makes me feel pretty unimportant... I'll wonder if he'll even remember my name. And there's always the fact that for me, I find a little inexperience charming.
