Why did I use Tor? Because a website whose FAQ said they don't log IPs (Slashdot) gave my IP to the Secret Service. The Service then came to my house with guns. Seriously.
(I showed them the comment, and they went away. The agents investigating did not actually read the comment before coming to my house to question me about it. WTF?)
Anyway, Tor is a necessity if you post content to the Internet. Although there is very little the legal system can do to you in the US for your protected speech, they can still fuck up and show up at your house to harass you. Use Tor, and they end up in Siberia instead.
Guess I was right!
http://metrics.torproject.org/graphs.html#recurringusers
Plenty more graphs and stats on that page. Also read this for information about the type of people who use it:
Tor is never going to be used by tens of millions of people. It doesn't need to be used by tens of millions of people to serve its purpose and be successful.
I'm not sure why they only present that small subset of countries in their stats. I wish they'd provide more comprehensive stats.
Now, if you fake the UA with something very common, turn off most Javascript, and encrypt your hard drive in a deniable manner, then you are OK. (One of my side projects is to make the deniable encryption even easier for web browser history.)
Cookies are per session. I use Firefox with Tor-Button.
In the worst case there is "someone" who does the things I do. But no-one does connect that to me. You could do complicate analysis and pinpoint my demographic through that but no-one does that.