-----------Update after comment by Ilya Bogdanov-------
Well, Ilya Bogdanov provided an example which gets more to the heart of the matter. So I'll flip over my cards and describe a real conjecture.
Conjecture: Suppose that $f \in {\mathbb Q}(x)$ has no poles in the closed interval $[0,1]$. Then the sequence $(\Xi^n f)$ stabilizes for $n \geq N$, where $N$ can be bounded in terms of the degrees of numerator and denominator of $f$ together with the heights of the coefficients of $f$ (in reduced form).
This is what I had in mind asking the question... trying to figure out how to quantifiably estimate how the sequence $(\Xi^n f)$ behaves (number of zeros, etc.) An effective proof of the conjecture would give new estimates on irrationality measures of logs of algebraic numbers, I think. And it fits nicely as a simple case of the Kontsevich-Zagier conjecture about periods.
Ilya Bogdanov drives right to the simplest interesting case, which seems important to understand. First is the sequence of graphs for $1/(1+x) - 0.7$ (a function in ${\mathbb Q}(x)$). $1/(1+x) - 0.7$ after applying $\Xi^n$." />
You can see that just a few iterations suffices to show that $\log(2) < 0.7$.
Next is the sequence of graphs for $1/(1+x) - \log(2)$ (using ordinary floating point operations).
$1/(1+x) - \log(2)$ after applying $\Xi^n$." />
You can see that the graph crosses the x-axis, through all of these iterations, as Ilya Bogdanov suspected. It doesn't go against my conjecture, but it does suggest that something beyond a bit of analysis of real-analytic functions is required. Also, note the changes in the y-axis in the above sequence of graphs... it seems that each graph gives about another "bit" in the approximation game.