I feel your pain and sympothise but unfortunately I'm in this exact situation and I'm doing it the long way and it's working.
I have 15,000 listings, real estate, and the pages are not optimal for spidering, so we changed them and are in the process of removing the 15,000 old pages and indexing the new ones.
First I redirected them to the new pages using the 301 but that only made thousands of pages become unavailable because they were passed over.
Then I used htaccess / mod_rewrite to change URLS and send the spider to the new friendly pages. THen I removed the old sitemaps, created new one's, submitted them to google, and we're off to the races a few days later.
So far I have 5,000+ of the new pages indexed and returning the new, expected traffic. The older pages are being removed because we setup the robots file to take care of that.
We have seen a slight traffic decrease but that was expected. GOogle will only cache for so long on your site, if that means caching OUT old pages and marking them off that's what they do. THat can take a few days but as long as you can verify google is visiting your site multiple times per day you shouldn't have a problem getting rid of the old and in with the new.
Again, that all depends on where the majority of entry pages to your site are coming in on. If less than 50% are coming in on the "/" or home page then you may want to try and split it up into 4 sections, 1 per week or something. THat way you don't see the decline as much and it's over a longer period of time.
That was my mistake, I did it all at once but I HAD to. the old pages had almost 4,000 lines of code before the first human word and they were covered in Ajax.
On to better things, getting those new pages in order so they can produce even better online.
Good Luck!
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