ok this is what I figured out, the random task first appears in your tool bar after you drop seeds on a neighbor (complete mutant sheology part 2), when I went back into my town I got the dialogue about SideShowBob but no exclamation point popup window, just the icon snuck onto my toolbar (it's a red toolbox rectangle thing)
in three games I've seen the first random task be the 16 hour corn earning task and one of the shorter fertilizer or corn jobs, these are all tasks I would be running anyway.
basically the random task is just ensuring people are sending characters on the corn fertiler earning tasks (& even though I dislike the 16 hour task length, I'll keep Quimby on jt since he doesn't have a shorter one
when you enter your town, see how long you have on the random task, clear it and then resynch your town before you clear the slightly later ones (maybe you'll get a followup job that you can clear in a minute or so)
the op suggested that you space the corn fertilizer tasks out with a larger time gap but frankly I try to minimize time in town (& want to get corn fertilizer faster than spades)