I used Trac fairly heavily in the 2006-2008 time frame.  It was nice.
My main problem was knowing when to create a new Trac instance and
when not to.  Much like source repositories - there are many ways to
organize.  Being able to search only one Trac project lended to
department Tracs rather than Trac instances for projects.

My other issue was Gantt charts.  I (having basically no python
experience) hacked up Will Barton's TracGantt plugin.  I made some
changes that I liked.  But a year later TracGantt kept me from
upgrading Trac -- the plugin didn't work and I was not able to put my
time into it.

A bit over a year ago, I jumped on Redmine.  Great..  It has nested
Projects and Gantt charts!  Sweet.  I put alot of effort into setting
things up.  I decided it wasn't magic and went back to Trac and just a
few months ago put Redmine into production again.  (are you getting
dizzy?  My new little company is!)

The trouble is, I really hate Redmine. I've mucked with the CSS so it
looks like Trac more.  That helped - I like indenting under headings
etc.  But it doesn't fix everything...  things I don't think I can
live without (that Trac has):
  - macros (an amazing assortment)
  - sane wiki markup
  - <code> tag that is sane, I really can't believe that textile is
popular
  - simple menus, new users know what to click on
  - pretty urls:  proj1.example.com proj2.example.com
  - defaulting to the top wiki page instead of proj overview

I've come to the conclusion that multiproject support probably isn't
worth it.  Which leaves me with Gantt charts as being a hang up.

We would be willing to contribute to some kind of bounty for good
Gantt support.  I really liked the mirroring of tickets that TracGantt
did in the old days - it was fine for me.  Basing it on Milestones
might be fine too.

I think I'm coming back...

Thanks in advance for comments on Gantt,
Scott

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