What are your thoughts on Ubuntu vs Debian with respect to functionality and he support (laptops in particular)?
I have used Ubuntu at work and in home for a while now and things have been surprisingly free from hassles. I don't mind moving to Debian if things work as smooth as now.
From my experience, as long as you choose the "nonfree" ISO [1] to install Debian from, you should be fine. On the default "free" iso my Wi-Fi didn't work while on the nonfree ISO everything was fine out of the box. Debian these days also has the "live and nonfree" ISO so you can test everything out before installing.
I've been owing Dell for quite some time now, and on Dell machine you need it for the wi-fi and graphics cards (if they have a nvidia, for instance). Don't know much about thinkpads, sorry. But, people lots of people from /g/ use it, and they usually use Gentoo, meaning they compile it from source (almost).
You can use the free version of Debian and install what you need later. But as I was saying, if you're installing on a laptop with no ethernet cable, non-free is the way to go.
I have used Ubuntu at work and in home for a while now and things have been surprisingly free from hassles. I don't mind moving to Debian if things work as smooth as now.