Meno – thank you for responding to Boyswork for me. I would also say that the answer to #1 is the same as the answer to #2.
Until now, I was always in favor of (or at least not against) boys and girls meeting on their own. I think I may have even written things to Rebshidduch at one point to that effect. However, from things that she subsequently wrote, I realized that it’s probably a very bad idea for her (and maybe for many others, especially in her age range). But again, you are coming in the middle.
I will just say that it has absolutely nothing to do with what other people think. It has to do with the fact that for many people it is beneficial or even necessary to have some kind of older, wiser go-between for these things. I know a couple who met on their own but chose an older, wiser person to be their shadchan, and it greatly helped to facilitate the shidduch.