A serious problem we have in our company, menttes work just with Plone, is how expensive is to add/train new developers. Is very hard to find python or zope developers out there. So, we've to train every new person in all the stack, and this is a big investment for a small company.
I think 6 months is par for training an existing developer to be a good Plone developer. I have been pleasantly surprised though by a friend who needed only 3/4 months before he could deliver good products.
But... it is a bit long. Plone 3 worsens the curve (sorry, I know we have component architecture and it is more correct, but it is true.)
At Upfront we're all subcontractors. We all had to get up to speed mostly by ourselves and show that we can deliver. That means the risk run by Upfront is smaller. The flipside is that this model only works for people fresh out of college, or people in mid-career wanting to change careers. And they need the right personality for Plone :)
I honestly think the only way to "win" is to make Plone easier to customize. I don't think marketing will help much, although I did notice Limi on some panel of 10 which made Slashdot's front page. I'm sure he spreads the word.
I've noticed a few tools which will help us win. Grok is going to make things easier. Argo+ArchGen is awesome for developers. We're looking at Deliverance right now as a styling solution. And then the whole new generation of tools which enables TTW development. And KSS is excellent.
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