E.g. the program goes through a state that is effectively 2DES which enables a meet-in-the-middle attack which allows an attacker to jump into the path at that point and dramatically reduce the search space for the next or preceding block etc?
The key and IV for every single round are derived from a keyed hash of the CVM's current state. This state is a cryptographic digest of the entire operational history up to that point.
So, even if a path structurally resembled a weak cipher like 2DES, the rounds would not have related keys. Each step is effectively a fresh cipher instance with a unique, unpredictable key. A meet-in-the-middle attack is not possible because there is no "middle" with a key relationship to exploit.