I've chosen TypePad to host our new blog. We'll likely go with the Plus version for $9/mo at first and then upgrade to Pro if we need it. I like their features of tagging/categorization, 3 blogs supported, photos and non-blogging pages, log files, and file uploading. From a negative side, TypePad doesn't support captchas nor searching. Eh, hit Technorati for search!
The only downside of Plus in our situation is lack of multiple author/poster support. However, I can field all postings at first and we'll upgrade to Pro if it becomes problematic. Or, we could share account credentials for a while. I really want to make sure he's well-versed in how a blog works and how to administer it. This is one of my primary goals.
[update]: After comparing Basic and Plus, I see only one difference: Basic hosts only a single blog. Well, we're only creating a single blog. Otherwise, they appear identical. We'll go with Basic for now.
Oh, and BTW, I'll stop calling it "New Blog" as soon as we've chosen a name. Maybe I'll call it SBOB (Small Business Owner Blog) for now.