Tilmann,
Windows-1255 and ISO-8859-8 are virtually identical, differing only in a few characters. So they're basically interchangeable. That said, Tcl (and HTTP) do recognize the differences between the two, and support both (as cp1255 and iso885908 in Tcl).
I'm convinced at this point that the problem is in the reading of the file on the AOLServer side. AOLServer/OpenACS seems to assume that ADP pages are all encoded in UTF-8. If I can somehow change this assumption, my problems will be solved. Until then, AOLServer will continue to read every 8-bit character in my file as an illegal UTF-8 character, and thus barf on every Hebrew character in there.