Thanks everyone for all the great input. From reading everything here, at this point in time it's probably not even worth trying to convince him otherwise.
We are a very small company which is why the company itself is not issuing ANY device WM or BB. So Aroc hit the nail on the head with the fact that right now the company can tell us to purchase our own device and plan if we want to and to get something that is WM or BBConnect compatible because that adds no cost to them.
I do know that he had some misconceptions on how BB's worked. I didn't have the conversation directly with him (another of my co-workers did) but I believe he thinks that the only way to use BB's is by using a hosting solution. He mentioned that one of the reasons that he's strongly opposed is that all of your email gets redirected to another server outside of our company. Which for us would not be the case. So one of things that I wanted to do is gather the facts and inform him.
I think for now I will have to wait and see if it seems that the company is going to start issuing devices and then jump in and pitch the BB solution to him. Based on Arocs above post, #1 would be a very strong argument for us since we only have 2 admins that support everything. Also, I missed the boat on #3 since we used to have 2 owners and one of them insisted on having a BB (which is why I thought we already had BES when I got one). Now we have 1 owner (the boss we are talking about here) and he is anti-BB :(
My reason for wanting them to go that route is that I've used several devices now to get my corporate email and so far I've liked the BB the best (and I'm not even able to use it at it's full potential!). It's a lot of little things that make me like it more so I'm not going to get into all of them.
I guess at the next happy hour when the boss is around, I'll bust out my eye catching Pearl and start playing with it. He'll get gadget envy when he glances down at his ginormous Treo and he'll ask me what phone I have. Then I'll lunge at him and start blurting out the sales pitch for BB's
It always helps to have a plan, right?