Anna, the evening outfit is really terrific. I think the color and the silhouette are so you! Amazeballs indeed!
Regarding the traffic on WiW posts, I've wondered too. As a new member, I have not started too many conversations, but I have noticed that the posts in which I explicitly ask folks to share experiences or opinions (or more recently, reassurance) get more traffic.
I don't want to necessarily assign a higher value to more comments -- it doesn't seem like an appropriate metric because there isn't a 1-1 correspondence between traffic and comments. BUT the forum does rely on crowdsourcing, and more comments = more data, and therefore more helpful in making personal style decisions.
At the same time, I don't often comment on your WiW posts 'cuz they're almost always the perfect combination of edgy, chic, and so put together that I aspire to that I am usually a little too awed for words. I always read the WiW posts because that's where I'm learning about how to fine tune my style, but I don't always comment. Plus, as others have mentioned... this forum gets an unbelievable amount of traffic too and it is easy for posts to get buried. Like Jonesy said, there isn't a right answer, and you should do what feels good and right to you. And embrace the fact that different things will feel right to you at different times.
Regarding the online dating profile, I do like #5 as one of the pics. I met my husband online, and my experiences with online dating persuade me that it's important to use pictures and words to your advantage to convey not only what you look like but also who you, and what spending time with you might feel like. This picture tells me that you like outdoor adventure, and if that's something you want coming across in your profile, go for it. (A picture of you dressed for the opera as well for the same reason? It's so hard not to be compelled by a woman who can go from sailing to opera in <24 hours!). I agreed with what others have said about showing your eyes, but I'm also assuming that this will not be your only profile pic and that there will be others that do.
Sorry about the long post, BTW!