I think it would be a tough decision for me, only because you stated the Roofer said all the women want to meet/know him. So it seems to me he is probably so use to the women hitting on him. I like to be the one who is different from everyone else, so I would probably prefer him to approach me. That way I would know it wasn't just because I was one of many who made it easy and asked him. But I would send out the signals. If a guy is interested and you have sent out the signals, he is going to act upon it.
What's the difference between hitting on someone and putting out "the signal"? Just what is the signal?
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It's a situation of you having an opportunity and not letting it go. Even if it doesn't pan out you will feel better that you tried versus pining about a missed opp later.