uhm. Technically having more than one instance of mssql running on the same 
ip is possible (multiple named instances) but it involves a totally 
different connection handshake. 
If you don't specify different port numbers, you can still have them 
"dynamic" but you have to resort to have SQL Server Browser running on the 
server and specifying a connection using the "odbc connectionstring" 
notation (mssql://{Driver={SQL 
Server};Server=hostname\instancename;......}), that will trigger that "new 
handshake"....everything works fine, I use it every day.

-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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