Neat! I sometimes play around with the idea of reverse engineering and transcompiling a tiny game that I think was probably written in Turbo Pascal 4.0. Maybe 4.0 supported optimizations, but this program seems to have been compiled in a debug mode. (At least, it seems to have no optimization, and has the default {$S+} stack overflow checking at the start of every function.) The lack of optimization makes it (and perhaps other programs written in Turbo Pascal) a really attractive artifact to experiment with transcompiling. When I realized that only the first segment was the actual game, and the other three segments corresponded to standard units used for I/O (etc.), which could be harder to analyze, I realized I could just omit those segments and replace them with new functions suitable for the transcompilation target. Maybe some day I'll get around to finishing it.
Good luck!