Tor offers a lot of anonymity but it's critical that people understand how Tor anonymity works. Your traffic is routed through three random hops that strip your info and the weak link in the equation has always been from the last relay to your target site. If you use
https everywhere (a great extension from EFF) then you pretty much have all the anonymity you can ask for. Now for some landmines....
You need to be careful about leaving breadcrumb trails. The busting of the Silk Road founder was a failure of the human and not the technology. It's probably best to never do any kind of authentication if you can, or use user names that are similar on Tor and non Tor networks. Also be wary of the browser bundle from Tor. This bundle is the subject of special interest by FBI and they are constantly trying to exploit whatever version of Firefox that it uses and was recently successful.
If you want to get on Tor you can always do it the easy way by using a router that has Tor embedded in it. I recommend
PAPARouter because it's inexpensive (less than $100.00), allows you to anonymize several devices at once and best of all it has exit nodes hard coded into it that are not friendly to US or the US intelligence machine. Given all the uproar that other countries are having with U.S. spying, making your last Tor relay outside of the U.S. to your target site is great security and using https would be massive protection.
I included a couple of other links that might be useful.
TOR AND HTTPS PAGE
https://www.eff.org/pages/tor-and-https
FBI exploit using Firefox Bundle
http://arstechnica.com/security/2013/08/attackers-wield-firefox-exploit-to-uncloak-anonymous-tor-users/
