That sounds plausible. There isn't any preference you could set which would cause a delay, unfortunately, so you can't easily test your theory. (And I can't reproduce the problem to test it myself.)
It would be helpful to have the diagnostic info from a connect/disconnect cycle done manually (i.e., not when the computer starts) -- please follow the instructions at
Read Before You Post.
One thing you could do as a test would be to set your DNS servers manually (in System Preferences / Network) to, say, Google Public DNS (8.8.8.8, 8.8.4.4). That would rule out certain types of problems.
After you've done that (and assuming it fails in the same way), I could build a test version of Tunnelblick which includes a 30-second delay before launching OpenVPN. If that works, then we can figure out how to make that delay customizable or if we need to add logic to wait until the Internet is reachable before starting OpenVPN.