I've never had any problems with connecting my BB to my Mac. I use MissingSync, and I am also able to transfer pictures from my BB to my Mac via bluetooth and vice versa.

I know you had your heart set on an iPhone, but there are plenty of people out there that hate their iPhones, and I knew several people that have switched from the iPhone to a blackberry.

You can get a 1GB SD media card for cheap, and I would recommend getting one if you plan on putting music on your phone. Even if you didn't want to put music on your phone, I'd still recommend one if you take a lot of pictures.

For themes, I just stick with the default T-Mobile one and change the wallpaper. No matter what, you're never going to get your BB to look as sleek as an iPhone. That's just one advantage Apple has over RIM. They have better designers.

What kind of trouble are you running into when you try to connect your BB via bluetooth for sending photos and stuff? I can try to help you.

Really my only complaint as a Mac user when it comes to my BlackBerry is the inability to install applications that don't have an over the air option. I'm looking into a workaround at the moment, though.