I have no problem starting with free drivers. Right now, I have Debian stable installed in all my machines (including those of my friends and relatives). I always use the netinstall image so, as you know, I end up with an almost 100 % free software system (well, in certain machines, this is not possible and workarounds are required). I am not asking to have the proprietary drivers in the installation CD.
The question is that some distros, before releasing any upgrade, try to take into account all kinds of situations, including the users with proprietary drivers installed. Others, follow the philosophy of "we just don't care about you because you are not representative/pure/knowledgeable enough for our standards".
To be honest, I am happy enough with Debian Stable. Only every so often I need a new feature that is only available in more recent versions of a program. If there are few, non-essential dependencies, I just pull the new version from Sid repos. Otherwise, I compile it from source. The problem is that, towards the end of the release cycle, Stable is really old and so you end up with a hybrid (stable-unstable) system. Another, related, problem is that certain developers use only the most recent version of libraries (even development versions), which forces you to be always current in order to compile their code. That is why I would be interested in a Sid-based distro which is stable enough so that you can spend 99.90 % of the time working and only 0.10 % fixing regressions and other issues after upgrades. But maybe this is impossible and a hybrid system actually offers the best trade-off. This is what I would like to find out.