Molly, I'm an estate planning attorney, and end up with similar issues.
What I would do is something in between what everybody else said.
Think of all the subtasks for that client, from the client's point of view. Some are related to one goal or outcome, some are completely separate.
Like for example, I am working on a sale transaction where I have to draft a pile of different sale-related documents, work out of the appropriate date of value for the appraiser to use and get the appraiser going, and draft trusts to be used in the sale transaction (which will be sent to the client separately from the sale documents). I also have to do that client's revocable trust.
For me, I would have the following next actions:
1. Draft revocable trust. That stands on its own, totally unrelated.
2. Draft irrevocable trusts for sale. Although it is related to the sale, it can go forward or get stalled out somewhat independently of the other items, and it has a different goal. The goal is to get sent to the client for review, and it will go separately from the sale docs.
3. Draft sale docs. Even though this may take 40 hours to draft, and have lots of smaller components, I don't break it up, there's no point. I just work on it and plug away when I can. The next step (give to partner to review) won't happen until ALL the sale docs are drafted, so there's really no point of having a separate NA for each doc, unless I want a way to track which ones I have already drafted or delegated to be drafted or whatever.
4. Appraiser stuff. Although this is also related to teh sale, it is sort of a separate side track to the document preparation. At different points in time, this NA will be titled:
"Smith: Appraisal: Draft Request for Proposal";
Smith: Appraisal: (wf bids back);
Smith: Appraisal: review bids;
Smith: Appraisal: figure out valuation date;
Smith: Appraisal:review appraisal; Smith: Appraisal: (wf revisions by appraiser) etc.
I just keep changing the title of the NA as it winds its way through the system. (And in the note portion of the NA, I keep a few notes on status so I can CYA later or find my place if I forget what's going on.
So think about how the various pieces are related on a timeline, and which ones are closely related versus only slightly related. I'm assuming the letter to tenant is about the complaint, so those would go together; you can't draft the letter until you understand what the complaint is about. Rather than putting 'Draft letter to tenant" on your @waitingfor list, I would put it in the note section of "review complaint." Your NA would be:
CLIENTNAME: Complaint re smelly dumpster - review complaint.
And in the note section:
12/20: PartnerX assigned to me. Need to review complaint. Then, need to draft letter to client.
12/21: gave draft letter to partner X.
(When Partner X loses the letter and comes down the hall to yell at you for not doing it, you can easily point out that you gave him the letter on 12/21, rather than fumbling around looking foolish because you can't remember whether or not you gave it to him (I'm always forgetting stuff like that). Sometimes this can backfire, obviously! ;-) But more often than not, they're impressed that you're organized.
Hope this helps and didn't put you to sleep - sorry to be long winded!
Taxgeek