Let me give you a discription of the compiler and then you can tell me if I understand everything correct.

You have a interpreter that for every basic block starts to record a trace. If you walk in to a basic block (or codeblock) the X-time with the same type you compile it for that type and you set a typeguard. Now everytime the interpreter goes trough there again it does a typecheck then either keeps interpreting or jumps into the compiled block. So if you have basic block in a loop you have to typecheck every time you go threw the loop.