Scott,
Do you think the Bret Hart push should have started sooner? They clearly always had plans of pushing him solo, even when he and Anvil were competing for the tag titles. I feel like they should have just had Demolition retain at SummerSlam and built up to them dropping the titles to newly-arrived LOD. Bret could have started his push right after SummerSlam '90. Maybe do Perfect-Bret for the IC title at Mania 7 (with someone else insulting Boss Man's mama and such) AND a re-match at SummerSlam '91.
That was absolutely the original goal. The whole point of the phantom title switch was that they fired Neidhart for cost-cutting reasons and were 100% ready to proceed with the Bret push. But then they changed their mind and un-fired Neidhart. As you note, they probably shouldn't have bothered. Building to Demos v. LOD at WM would have been pretty awesome, whether or not Eadie was involved.