I don't think the logic in this episode is as tricky as it appears.
Let's assume that each loop for the Enterprise lasts 2 days, just for the sake of argument. From the D's POV, it starts with the poker game, Sickbay calls, Bev goes to sleep and hears voices, and in the morning they have the collision. The collision resets everything back to the beginning.
For the Bozeman's point of view, it would start before they travel through time. A bunch of stuff would happen, culminating with the Bozeman being drawn through the wibbly wobbly time wimey thing and colliding with the Enterprise. This resets the loop, sending the Bozeman back to the beginning - 80 years ago (or however long ago it was). But it would take the same length of time for the Bozeman to go through one entire loop as it did for the Enterprise. The only difference is that since the events that happened to the Bozeman included a trip forward through time, the Bozeman's loop spans a longer period of time that the Enterprise's loop.
But the two loops (the E's and the B's) both take the same length of time, and since we saw the Bozeman in each of the E's loop, then the Bozeman would have been through the loop the same number of times as the E.