http://webdocs.cs.ualberta.ca/~kondrak/papers/thesis.pdf
I found this bit interesting:
"An early paper by Smith [1969] provides an example of a derivation
program
that deals with a much larger time distance. The goal was to derive
modern Russian
from reconstructed Proto-Indo-European forms. These two languages are
separated
by at least 5000 years of mostly undocumented changes, as compared to
about 1500
years that have passed since Latin split into Romance vernaculars. Out
of the total
of 650 Proto-Indo-European etyma that were examined, almost 90% have
left no
re
exes in Russian, and so could not be used to verify the correctness of
the program.
Of the remaining 69 etyma, the generated form exactly matched the
corresponding
Russian word in only 9 cases, which prompted Smith to rather gloomily
conclude that
\historical linguistics may have grossly overestimated the
exceptionless character of
sound change." The poor performance of the program, however, was most
likely also
due to the incompleteness of the implemented set of sound changes.
Appendix B
contains some results of my implementation for modeling the
phonological evolution
of Polish that contradict Smith's conclusion."