Alrighty then. Hopefully I didn't screw the spreadsheet up, but I'm pretty sure these are accurate!
Important facts before we start:
the total number of contests run so far is 65, and the
total number of winning stories is 71 (due to tied months).
Entries before first win for all winners:People who have won with their first entry account for 40% of all winning stories. Repeat victories only account for 31%, first-time winners 69%.
Regulars who have not yet won a contest:Obviously there a huge number of contest entrants - 242 - but only 47 have entered 5 contests or more. Of those, only 14 have not yet won one (30%). They tend towards the lower number of total entries, with a couple of outliers. In other words, if you consistently enter the contest, your likelihood of having won one increases. Duh.
Total wins and total entries for contest winners:At a glance, it looks like these stats show that the people with multiple contest wins have a) entered many times, and b) won within their first three or four entries, with one exception who won with their sixth entry. I'll let someone else work out if these have any more insight to give!

I dislike the anonymous posting idea because it'll basically kill off the discussion thread entirely, as if people say "yay, finally posted!!" You'll know it's them.
People posting "yay, finally posted!!" isn't exactly a discussion though. There's arguably more to discuss if the identities are not known - who the author of each story is, which regulars have entered and which haven't, etc.
It also means I can't re read and edit my own story once it's submitted without sending X many emails to the moderator in charge.
It's not difficult to hold off on submitting until the final day or two, which would mean you'd have just as much time to get edits in.
It also means we can't talk about the ideas we had or misgivings we encounter. Like "hey I've decided to write in present tense and this is bothering me, what do you think?" > only one present tense story means it's yours.
Depends on what's being discussed. In that example, you could easily say "I'm thinking about writing in present tense, what do you guys think of it", which leaves it unclear as to whether or not you'll actually do so in the end. Just requires a bit of thought about what others will understand from your comments.
The critic thread is pretty dead too, so we'd never talk about our stories basically...
Nothing stopping everyone discussing which entry was written by whom after the fact, which could actually be a pretty interesting discussion, especially if people note down who they originally thought each story was written by.
I think that implementing a forced review time for example, to make sure everyone gets a constructive critique, would be way more appealing (at least to me) than an anonymous thread.
As in people would be forced to critique others work? Doesn't sound good to me. If people are interested in critiquing, there's already a thread for that. If it's mostly empty, then it means people
aren't interested, so forcing them to critique means you're forcing them to do something they don't want to do. Don't see how that could be anything but an awful idea!
I'll completely recognize Jmack, rukaio or m3m or tebakutis entries. I'll also enjoy working on the stories less if we can't talk about them. The liveliness of the discussion thread is the only thing that half convinces to keep working on this month's idea.
People rarely give away everything about their story while discussing it though, so it's a matter of keeping things more vague rather than not discussing at all!