kazman -
My guess is that you're not going to get Bruce to answer your "will DL consider" and "does DL realize" questions. But he has answered your #2, 3 and 4 questions.

2 - Yes, "six Platinum Medallion Upgrades" is one of the ongoing PM benefits, [unless DL changes PM benefits in some future year].

3 - "Platinum Medallion members will be able to upgrade from L, U and T fares from May 1, 2003"

4 - Regarding automating the upgrade process, "We are working on this – please watch for future updates regarding enhancements to the upgrade confirmation process."