OK, I'll take a shot.
In terms of your bag making it on your first flight, I assume it would increase the odds to the extent that bag matching is done correctly. But in terms of your bag misconnecting...my understanding of the bag matching rules lately has been that you must only travel the first segment with your bag, which can go without you from there. I've had recent domestic trips (all since 9/11) on which I was able to request that my bag be checked directly to a different destination than the one on my current itinerary, and the agents mentioned that requirement to me (usually as part of talking themselves into the conclusion that it was legal).
Nevertheless, hope someone else posts if they've heard that this will also be tightened up come Friday (or whenever the extension will be).