i'm having a quite similar issue atm and i'm unsure what to do.

same thing, Legacy MSSQL Database with windows-1252 charset (so iso 
compatible) on the legacy tables, and the Rails app purely using UTF-8.

i had no problems with encodings while using the sqlserver driver in ado 
mode
and setting:
WIN32OLE.codepage = WIN32OLE::CP_UTF8

but unfortunately the ado driver is leaking memory so badly that the 
mongrels need to be restarted every 2 hours.

when i switch to odbc mode, the memory leak is gone but with ODBC the 
codepage setting doesn't work anymore, so i get messed up texts from 
those old tables.


so i have to choose between the 2 evils:

1. memory leaking app with proper encoding
or
2. stable app with garbled text
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