First of all: Sorry about the delay. Hope you’ll enjoy the last part.
Upgrading strategies
Umbraco has “always” been quite easy to upgrade. A developer never thinks ”oh no” when someone asks for an upgrade. It’s usually a task completed within one hour, and includes a few simple steps. This said, you will probably run into some issues regarding community installed datatypes and modules (Umbraco doesn’t provide the full package of required datatypes, like Sitecore, and unless you are building a really really simple site you will have to build your own or download extra from the community). These are not supported and not always kept up to date, which can give you problems when upgrading.
Historically Sitecore has been a struggle to upgrade. It sometimes included creating two websites on a workstation, copying custom source code from one to another, etc. However, in the past year Sitecore has released the Upgrade Framework which eases the process substantially. It’s a wizard based tool which analyzes the solution and recommends some necessary tasks to complete the upgrade. If the wizard can’t access some files, it generates a batch file to run manually. I think Sitecore might be moving towards an update service, like the infamous Windows Update, but this is just a hunch. It’s now just as easy as upgrading Umbraco – at least between minor revisions.
I don’t know if an upgrade from Sitecore 6 to 7 will be just as painless. But again, upgrading from Umbraco 4 to 5 will probably be just about impossible…
As of now I think the products are equally strong or weak in this area.
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Sitecore Update Installation Wizard | 
Umbraco Upgrade Wizard |
Multi developer setups
Sitecore have made some really big enhancements during the last couple of years, including Item Serialization (dumping the database to files on the hard drive) enabling developers to share the data structure just like source code. Sitecore has no issues concerning multi developer setups – anymore. I won’t go into a description of the setup; however the concepts involved is briefly described in another blog post (http://blog.created.dk/post/Optimizing-Sitecore-development.aspx).
Umbraco is still lacking the last touch in regards to environments with multiple developers. There are methods to circumvent these issues; however none of them are really graceful. It usually includes a shared database and agreements to work in different structures.
In the near future
Well, Sitecore continues to stabilize the platform eliminating the last couple of weaknesses within the next year or so. This includes Sitecore codename Twin Peaks , focusing on scalability in production environments (Editorial cluster, Live mode clusters etc). Another release (“Halo”) is planned by the end of 2010, however this is mostly an optimization release.
Umbraco has begun planning version 5 (codename MVC). They’ve announced that it will be available by Q1 2011 (I somehow doubt this, though). As the codename reveals the plan is to implement the Umbraco Core using the ASP.NET MVC Framework. How this will turn out, only time can tell – but the overall strategy from Umbraco seems to be stabilize and standardize. Not a bad idea…
I don’t see Sitecore and Umbraco getting closer to each other in the near future. Sitecore won’t move focus to smaller solutions, Umbraco won’t move to Enterprise level.
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Sitecore Product Roadmap | 
Umbraco Documentation Wiki |
My conclusions
As you may understand, I can see a lot of differences between Sitecore and Umbraco. The biggest being that Sitecore is a Development platform (including an excellent CMS) where Umbraco is merely a basic CMS (although a very good one). Sitecore can be too complex, where Umbraco can be too simple…
If I was to give my take on the where I see the two products main business area is, it would probably look something like this:
Sitecore is an Enterprise CMS / Development platform focusing on medium to large-scale solutions. This should be evident to most, looking at the product and the roadmap.
Umbraco is a very popular Content Management System with a very large and dedicated community. Their main area is small to medium solutions.
To get a grip of which system has the strongest appeal to developers, I did a small vote amongst developers experienced in both systems. The question was: “If you had to choose to work with either Sitecore or Umbraco exclusively for the next two years, which one would you pick?”
Result:
- Sitecore: 8 votes
- Umbraco: 5 votes