Hey Mike,
I have been following your posts with interest, as I imagine many other's are also doing
Maybe it's not the route you would like to take since the restrictions on redistributing software/updates have been updated/relaxed with OS 3.0 and the new SDK, and maybe it is a little too technical for some of your users, however, have you looked at the way WeDict Pro offers to download dict files directly to the iPhone to update its dicts? They download without a problem. Additionally, WeDict Pro has a built in FTP which is quite nice. I just uploaded about 600 MB of dictionary files to my iPhone using the FTP in conjunction with Filezilla downloaded to my PC. It was a painless process and occured without a single event.
I am sad to see that some of the features I was most hoping for in OS 3.0 won't be available on my 2G iPhone. What gives? It appears that the hardware should be entirely capable of MMS and A2DP. Is this a ploy by Apple to get people to upgrade to the more secure (read: more locked down) iPhone 3G and to make additional profit at the same time? Yeah, I am aware of yellowsn0w, I have re-jailbroken and re-unlocked my iPhone with every new firmware update that has come out for carrier choice as well as feature enhancements.
Oh, I am glad to see that you might be leaning back towards including flashcards in the inital release. This is a biggie for me since I already own the WM version of Pleco, with everything you have offered installed, and therefore do not necessarily "need" the iPhone version but instead would prefer it for convenience, such as for yanking it out of my pocket to study a few cards while eating my lunch or during a lull moment at work, etc....
Cheers!
Darrol