I and my company have just spent the last month or so evaluating Umbraco to see wehther it would fit our needs.
We were looking for an open source replacement to a basic in house CMS we had developed.
It was important that the CMS was in .NET and was easy for end users and developers to use.
It also needed to be customisable and extendable.
Umbraco ticked all these boxes and has an active and helpful community surrounding it.
However the documentation is not terribly complete or up to date which can make getting started rather difficult. particularly for more complex implementations.
Another weak area, is workflow and page locking, but this is being worked on in the commercial version and is really only a concern for larger scale implementations.
For getting to grips with simple sites The Creative Website Starter kit is excellent and gives you a good grounding in how Umbraco works and how to implement a simple CMS based website.
The most important thing to do before starting an Umbraco implementation is to plan your document types and content types. This is because once implemented it can be hard to change document types on pages you have already created and populated. CMS projects invariably live and die in the planning phase anyway so this is no different to any other CMS.
I've used many many different CMS platforms over the years: Immediacy, MCMS, Sitecore, Obtree, Reef, Reddot etc etc and I've found Umbraco to be stable, fast and extensible.
It has it's quirks and in some places lacks polish but overall it is an excellent CMS for small to medium sites and, with a bit of tweaking, for large site's as well.
We The Cogworks have settled on Umbraco and are now in the process of migrating our clients, on our legacy platform, to Umbraco as well as a brand new implementation.