(starting a new topic as this is a little wider than the original thread, hope that is OK)

I think it is clear that just letting OTRS handle it doesn't
really work and people need more support than just an email address
they can send things to and get back a lecture on Wikipedia policy and
procedure,

Well, respectfully I disagree - at least in part.

OTRS very often works. It is because of the work of OTRS volunteers there aren't more news articles featuring prominent people who have had little or no success with Wikipedia!
 
and judging by the number of attempts we see at setting up
for-profit consultancy services for this, it would appear there is a
market. (I think there is probably a market of companies and
individuals that would be happier paying even if they could get the
same thing done for free, just because they feel more confident in a
paid service.)

The problem with this approach is  that if you enter into a monetary contract with someone they have more expectation of a result. I'm not shouting down the idea outright - but it is much harder to turn around to someone and say "I'm sorry, but this content can't be changed" when they are paying you to do that... :D

Even if sold merely as an advisory service with no guarantee there would still be an expectation. (and there are also moral issues tied up in there; dangling the resolution of an issue in front of an individual, who is upset and vulnerable, for a fee..).

Selling advisory services on an one-to-one basis is too much of a minefield!

It would be better for a social enterprise of Wikimedians to be
providing that paid consultancy than some of the other people trying
to offer such services.

We do have to be a little careful here what with the current grumblings about COI etc.
  
I did try and draw up a rough business plan
for such a consultancy, and I think it could turn a profit. The big
unknowns were how much we could charge (I used some PR consultancy
chargeout rates I found online as a rough estimate) and how much
non-chargable work would be required in order to attract business (if
we get people just knocking on the door without any reals sales work
required, then it would easily be profitable).

Is this something you would be willing to share with us?

My thoughts are that you have the germ of the idea, but are taking it in a direction that runs into numerous problems farther down the line.

OTRS kinda works; I will admit I have seen some replies from Wikipedians that make me cringe at their bluntness. However this is not an unassailable problem.

I would tackle this idea in three ways:

* Invest in OTRS agents; run training sessions (we have already done that once I think...), write training materials etc.
* Invest in the OTRS software; it's not entirely fit for our purposes. The concept is not complex, and I feel it would be possible to contribute either to the OTRS software-base, tweak the existing code or even begin from scratch with a custom-built solution.

The third strand would be based on your thoughts about paid support. Rather than offer one-to-one support, I'd suggest training days and support groups (think; Wikipedia Anonymous :)). Based loosely on the format of a morning crash course in Wikipedia and an afternoon QA session, with editors around to help with individual issues.

Just thinking aloud.

Tom