So - management is looking to do a push to move towards doing unit-testing in all the applications moving forward - and eventually get into full TDD/Continuous Integration/Autom
I like the commitment and thoroughness you're expressing here, but my feeling is your adoption plan is going to take longer this way than if you started straight in, paired up and wrote some actual production tests. You'll need infrastructure anyway -- why not bootstrap your actual production code with a CI server and a TDD framework? (A lot of times this is a bigger pain point than learning "asserts." Get this part out of the way sooner rather than later). Then sit down and solve an actual problem with a fellow coder. Pick a simple bug or small feature and try to identify what the failing tests would look like and try to write them.
I like Hello Worlds for a brown bag lunch or something. But I can't think of any reason not to just jump right in and solve some problems.