I recognize myself in your situation. I’ll share my experiences below.
> So I'm trying to prepare a simple but complete todo list.
You already have, because you can’t make it complete. Start out with the
questions you posted. Pick one that concerns you more and try to fix it. Then
move on to the next one. Let it take time. Motivation and available time will
come and go. Things on your list might fade away before getting to them, and
others might be added during the time. Don’t worry about getting
“everything” done “perfectly” at once. Take it step by step. You’ll
learn lots along the way—and many things you cannot know before you’ve
tried them, no matter how much you read about it. Doing _something_ is better
than doing nothing at all.
> I'm still not writing from my free machine since I want to configure it
properly.
And you will forever unless you stop worrying.
> Everyday I read about some new thing to configure (like the default
Trisquel DNS server being google's).
See what I mean? Stop reading and get started! Then, when you feel that
you’ve come a bit along the way you could start reading and looking for new
things to do again. Otherwise it will feel overwhelming.
Don’t worry about feeling “I’ve should have done this straight away!”
and feel bad about having done something “wrong” for some time. That
always happens.
Also, what’s worse? Using a proprietary system, or a free one with
Google’s DNS? Do it in steps! One: Move to free system. Two: Move away from
Google’s DNS. If it takes a few weeks between step one and step two
that’s OK. (Note that as has been said earlier in this thread you do _not_
need to be worried about the whole Google DNS thing since that error has been
corrected for a long time now.)
> So what's you're overall privacy strategy, everyone ?
Improving just a little bit is better than not doing it at all. Bit by bit
you’ll get closer to your utopia.
> [lots of questions]
Great! That shows that you’re really into it, and you actually know a bit
about it too. Continue that way! Try things out! See what you think.
I hope anything of the above helps :)