Which one? These are nested loops.
She also only has her watch long enough for her meetings with Hugo, in New York, in 1953
While time progresses linearly through a year 1, 2, 3, 4 at the start of a new year in the Static streams, it starts again in the dynamic streams.
1, 2, 3, 4, etc.
So if you are sitting on December 2nd 1953, theoretically I can loop back to that date every year ad infinitum. I can wait 364 days and visit you on December 1st, or one week to visit you Dec 9th.
As long as Dottie has a watch, if Hugo tries to repeat Dec 2nd directly, she will know. He VERY specifically resisted that urge in the last chapter because he cannot afford her realizing he is looping his years, while she simply thinks in weeks.
@Jeff Burton did warn me that this might be a little complicated.
Hugo has had 10 chances at Dec 2nd so far, but he has only gone there once. This is the limitation of his side of the plan. What he is doing to counter this is he is visiting, studying, and picking apart the lives of everyone in the bar on the dates of the meetings. They have no memory of him, but he knows every aspect of their lives by this point. Information is his weapon.
Billy specifically, has a weakness. And Hugo is becoming Ruthless.