I've been playing a bit more with adding documents to my T-Mobile Wing. So far, it seems to handle Word docs much better than the old PDA (especially documents with pictures
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I managed to post a couple entries with just an image, apparently by putting it in a directory used by LJ Mobile. Sorry if I spammed anybody's Friends page before cleaning it up.
Edit: Now that I've confirmed that the post made from the Wing showed up, extending it and shifting it from private (just to avoid spamming people with a contentless test post) to public. After some initial problems, ActiveStync seems to be behaving itself.