I'm not sure if this qualifies as a bona fide tip (since it's actually only 50% towards an actual solution to the problem). That said, one problem I've been having with the GMail/Firefox Remember the Milk extension is that it does not always load when I arrive at my inbox. I'm sure that there's a solution out there somewhere, but again, this is about laziness.
I could, of course, run RTM from its website in my browser, but I like to think of it as a separate "application" from regular browsing, and want to zip to it via ALT-TAB. Plus my taskbar goes vertically along the left-hand side of my screen, so tiny bits of text description won't help.
As a "solution," I've started using a different browser for RTM. So while all my main web stuff is going on in Firefox, I have RTM in Internet Explorer, and the blue "e" icon in my task bar translates to my brain as "tasks," and the Firefox icon translates to my brain as "internet."
I know TWiT or Macbreak Weekly have suggested applications that will replace the browser icon with something particular to what you're using it for. But again, this is about laziness, and to that end, it'll work for me.