My own two cents on the Plone vs. Sharepoint topic:
Sharepoint is still geared more toward being a document management system that lends itself toward intranet sites rather than nice-looking public-facing sites, and it lacks the sophisticated workflow and flexibility in structured content types definition and management, as well as taxonomy management that Plone provides.

Sharepoint also provides much deeper integration with Windows/Microsoft-based apps, which only makes sense. People sometimes forget, though, that with Plone you can deploy External Editor and save Office files right from Word, Excel, PPT, etc. right back into the Plone CMS when you click the Save icon in Word, Excel, etc. PloneDesktop is another tool that provides a level of Windows desktop integration (file check-in/check-out, etc.) via WebDAV.

There is a helpful Sharepoint calculator that I ran across some time ago that can help you in assisting your clients in comparing the cost of implementing MOSS vs. Plone as well:
http://community.bamboosolutions.com/blogs/sharepoint-price-calculator/default.aspx

If a client is evaluating Plone vs. MOSS as DMS/Intranet options, then it can be a tougher call and MOSS is more compelling. For external-facing sites, it’s tough to beat Plone.

Also, in my opinion, while Plone can do what MOSS does, outside of some of the deeper integration features, Plone blows it away still for dynamic public sites – especially those with Web 2.0 / community requirements. The tool that is more similar to MOSS in the open source world is Alfresco (more geared toward document management.)

You might want to take a look at the comparison done on those two tools by CMSWire, as it might add to the conversation regarding Plone vs. MOSS as well:
http://www.cmswire.com/cms/enterprise-cms/sharepoint-vs-alfresco-a-platform-perspective-004549.php

-Ken

I hope you’ve been well. Sorry to just now be stumbling upon your blog post on this subject. There was a pretty nice in-depth account by one of the folks at Idealware.org that provided some insights into what situations they were more likely to leverage Sharepoint vs. Plone, Drupal, or other open source tools.

Idealware generally helps non-profits evaluate different types of software in order to get the most of their technology investments. They put together a nice, free evaluation report of free open source software (FOSS) CMS solutions too. I list both links below.

Here is the ‘Why Sharepoint Scares Me’ blog post:
http://www.idealware.org/blog/2009/07/why-sharepoint-scares-me.html

The open source CMS evaluation report:
http://www.idealware.org/comparing_os_cms/

They allowed my firm, Contextual, to redistribute their report at the CMSExpo that we sponsored/had a booth at this past Spring, so if you find it useful and contact them, you might want to do the same. The report was funded by all sorts (200+) vendors, received input by experts on each of the CMS tools reviewed, and is quite objective and pretty accurate in my opinion.

Their Reports and Articles section is a treasure trove, so I spread the word when I can.

-Ken

11. A good liar

“…poor support for “small” players (i.e. anyone outside the US and EU)…”

One great tip from a presentation I went to on running a successful CMS procurement was to find a company that ‘fits’ your organisation. And one aspect of that is the size of the company.

If you are a small business and you go to some large vendor they are unlikely to give you all the attention you need, you are just small fry to them. On the flip side if you are a massive corporation, you are not going to want to go with a one-man-band for support.

*This* is one of the key elements of Open Source, that there are hundreds of companies out there, from one-man-bands to large consultancies who can help you. So even within a single product you have a choice of vendors.

With Plone there are hundreds of companies listed on plone.net and probably the same number again not listed there. You can pick one that fits your business in terms of size, ethics, location etc.

At Netsight, we’ve referred potential clients on to other Plone companies we know if they are a better fit for them (and indeed one of our largest clients was referred to us by Francesco as we were closer to the client).

Again, it all comes down to choice. Open source gives you the flexibility to choose your development partner. And to change it. Should you find that for some reason the company you originally picked isn’t working out for you (maybe you outgrew them, or they are too busy, or just a clash of personalities) then you can switch to another company without having to change your technology stack.

-Matt