Hi,
the news is that a few 16bit apps crash in Wine, apparently depending on the gcc version used to compile Wine. This was known to affect copy-protected apps, but in the present case, copy protection is not involved.
perhaps that old wine-1.1.16 was compiled with Ubuntu Hardy, not Intrepid...
Indeed that is the difference: - Meine Traumburg (children game probably nobody knows outside Germany) crashes at start; - Caesar III from Sierra (mine is the German version) aborts before the second installer screen ("error 112") with no revealing error message or stack dump using a Wine compiled in Ubuntu Intrepid. They work fine with a Wine compiled in Ubuntu Hardy. Sorry, I don't use any newer Ubuntu (yet). Wine-1.1.16 and 1.1.34 behave the same.
http://wiki.winehq.org/GccVersions mentions that some versions of gcc miscompile some code relevant for copy protection. However the above apps are not protected AFAICT! (They are trivial to install on HD without the need for the CD at run-time.) So gcc (presumably) affects "regular" code in Wine. The winesrc/include/config.h file on both systems is the same except for one line about mpg123; that's why I believe gcc is to blame (or Wine does some 16bit assembly magic that's not supported by gcc and thus produces random results).
Hardy uses gcc-4.2 (Wiki page says "known to work/this isn't certain") Intrepid uses gcc-4.3 (Wiki page says "not tested")
It would be interesting to re-evaluate bugs.winehq for bugs with keyword "win16".
Regards, Jörg Höhle