Ok let me give you a small background of my problem. I am using a (very good) VPN service as I am trying to hide the fact that it is me (ip:....,name:....,etc) who is managing a particular website. I use VPN, sometimes tor, truecrypt etc, but my knowledge of these security tools is limited. Some time ago I did a couple of stupid things: like to speed up my connection I decided just to disconnect my vpn while browsing more specifically while using a yahoo email account. I did the same while browsing sites where I have a paid account. Now what I want to know: what are the realistic consequences of my behaviour for my anonimity status. I read in this forum that authenticating to social media destroys every bit of anonimity you ever had. Is this true, or is this just a worst-case scenario Would it not require a pre-established monitoring tool on the endpoint of my vpn, and a conscious decision of a monitoring human agent to follow up on these findings and ask for the network logs of these service providers. Is it not more likely that yes there are incriminating ip-records in databases, but as no one yet has any real interest in me nothing will be done with them?
I also sent pgp encrypted messages through yahoo. Am I now marked as being a suspicious character and how likely is it that from then on "they" will try to track me?