In regards to the Shark I think it made all of the sense in the world for them and also for us at the time (I believe we were leading the AL East), I take my hats off to the A's organization. The only thing comparable to that for us now is perhaps Cole Hamels if the Phillies are willing to eat salary as reported but I still couldn't see the Jays manning up and pulling the trigger (also I don't know if he's got a no-trade clause for here).
I agree with your Milone proposal, I think he'd be a great addition if we can usurp him from the A's but I think that would be a very difficult proposition.
I disagree with you here though, although I feel they are definite needs and especially going into the off season the Valencia trade and the return of Reimold, Lind, Lawrie, and EE as you mentioned should fill these holes. For the time being I think we need pitching help more, I feel we need a top 3 starter to bolster this lineup. We just don't have the horses right now to seriously compete in the playoffs (if we even make it there) unless we catch lightening in a bottle by having our supposed top 2 of Buerhle & Dickey play at their best and our young guns of Stro & Hutch play up to their potential consistently from here on out without any dips. It's a slippery slope imo..