orderby should be table's field not a conditional comparison
ref:
http://web2py.com/books/default/chapter/29/06/the-database-abstraction-layer#orderby--groupby--limitby--distinct--having-orderby_on_limitby-left-cache

for 2nd question: web2py auth.signature will cover to update value of field 
modified_on when user update the table, for any specific table's field 
perhaps you can use before or after callback 
ref:
http://web2py.com/books/default/chapter/29/06/the-database-abstraction-layer#callbacks-on-record-insert--delete-and-update

best regards,
stifan

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