Hi Sara,
Noting that I'm getting a bit more comfortable with the spooky correlation between "Questions On The Forum" and "Stuff I'm Already Working On This Week", I have another option for you.
Last year, I tackled this conundrum of "dedicated custom comment field" vs "natural flowing updates". Both have pros and cons:
Technically, the Last Update Note Text will always contain the text of the last update, regardless of who entered that information -- easy, but quickly replaced by any other Update, regardless of how trivial.
Similarly, the Task's Condition Update (as you mentioned) records the Primary Owner's last comment -- prominent, but quickly stale dated unless attended to in a timely fashion.
And from a Task list view (for Tasks, or similarly, a Project list view, for Projects), Updates are not easily editable unless you "go into" them, which (even if opening in a new tab) slows the flow of conversation
That final point is one of the biggest advantages for storing comments in a designated field (as Barry suggested): quick editability. However, in my opinion, and as per your current process Sara, the contextual advantages of using the Update feed makes it "worth the effort" to go into the Task (or Project) to enter an update.
But that still leaves the overriding concern unanswered: how can you "escalate" the most important Update(s) up to the Task or Project?
The solution I came up with was to add a calculated Text Field (on our standard Tasks Custom Form) called Task Owner Current Update. In its description, I wrote "This field is populated with the latest note entered in the updates section by the Task Owner (default assignment) that has been flagged with an asterisk (*)." Practically speaking, when the Task Owner was entering something within the flow of updates that she wanted it to appear at the Task Level (e.g. for Official Reporting Purposes), all she need do is preface the comment with an asterisk. To me, it offers the best of both worlds: the flow of the updates can continue contextually as the discussion unfolds, but the Task owner can easily escalate a particular comment "up" to the Task Level for summary consumption.
The magic, of course, is in the formula, which I'm happy to share here:
IF(Assigned To ID=Project.Owner ID, Project Manager Notes, IF(Assigned To ID=Last Note.Owner ID, IF(Left(Last Note.Note Text,1)="*", RIGHT(Last Note.Note Text,LEN(Last Note.Note Text)-1), Task Owner Current Update), Task Owner Current Update))
Note that to use this technique, you'll have to create the Task Owner Current Update calculated text parameter to a Task Level custom form, SAVE the form, and THEN copy in the formula, since it is self-referencing -- namely, if the Latest Update.Note Text was entered by the Task Owner AND starts with an asterix, overwrite the Task Owner Current Update contents with that Note Text, but otherwise, leave it alone. Effectively, it's "as if" notes could have custom data, as Eric proposed.
My homework, to get back to the spooky factory, is to expand on this concept by:
adding separate audit fields (who said this)
adding aging (how long ago did they say it)
adding "staleness" (e.g. making the text lighter and lighter as it gets older) to encourage more frequent updates)
to allow other one-character prefix functionality (e.g. * = overwrite, - = clear all, + = append, effectively allowing several important comments to "roll up" until cleared, etc.)
to repeat these concepts at the Project level, too
I hope this gives you some ideas, and if anyone's interested on how my homework turns out, please leave a comment here and I'll add an update another time.
Regards, Doug