You can't track this reliably. What you can do is set up accounts on the target services you're interested in, such as gmail, live, hotmail, yahoo etc, send yourself messages on those addresses, and see whether they end up in spam or not. Unfortunately that's still unreliable as every account has a different spam profile, so what works in one may not in another. What most of the inbox monitoring services do is have large seed lists of such addresses that they send a copy of your messages to, and report on the inbox/spam placement.
The "preblocking" is also very hit and miss. One way of doing that yourself is to install spamassassin on your own server and submit test messages to it. Again, this is not reliable as every spam filter is different - but a really bad result on a default config is a good indicator that your email looks spammy.