Do Microsoft use Outlook Contacts and Categories?

I have to ask as the contacts section of Outlook betrays some serious screwed-up behaviour. To start with there's supposedly a push away from using distribution lists and the "Select names" dialogue box in favour of categories and the actual Contact window.

Okay let's try that with something simple - a group of contacts some of which I'll categorise as "members" and the others remain uncategorised. I want to send an email to all the "members". To do this I need to change my contacts view to Categories, find the members section, click on that and then right-click and do Create|New Message to Contact just as I would a single contact.

Oh wait I can't as when you select more than one contact or a whole category Microsoft remove the Create pop-up meaning I have to go all the way to Action|Create|New Message to Contact. Of course I mean heck who's going to try to send an email to more than one contact at a time.

I now have a new mail message and all my "members" in the "To:" section Yup no option to Send them as "Bcc:" from the menu I'd need to cut and paste them in to do that.

Ah well time to send my email - oh wait I need to add in a couple of non-members who need to see this, but whom I don't want to give away their email addresses to the rest. Given I have both the Message and the Contacts window open at the same time it's trivial to find the non-members I want and drag them into the "Bcc:" section. Sure if I drag a contact into the message Microsoft will interpret that as to send the whole contact card, but dropping into a header section will mean just dropping the email address in surely.

Hah don't be silly it tries to paste the contact card in their instead.

There appears to be no way to add in any other contacts from the Contacts window to an existing message I could click the "Bcc:" button and use the "Select names" dialogue but a) I'm not supposed to b) it doesn't show the categories I'm supposed to be using and c) it won't search in the categories if they happened to have one.

It seems the only way to do this is to create a message to the "members" then create another message to the non-members you want to add, then cut/copy paste into the first message.... seriously that's the solution?

The dumb thing is that they've worked out that with multiple categories you only want to send a member of both one email. Sending an email to "members A" and "members B" where there's an overlap will only add one email in - so they got that bit right; how did they get the rest so wrong?