this would be best ran from your sql server (if you are running a sql server)
if you're thinking of trigger to 'trigger' the action then this would not work, as you need something to happen to the record to trigger it.... (thats the word trigger over used)
your best bet is to create a stored procedure to check, send and mark
i'd probably add a field to the db, either a bit field for marking or a date field to record the send date!!!
select all records to send where the datediff is greater than you specify and the emailsent is null / 0
loops are not good for stored procs but not sure how you'd send a mail otherwise but its something to consider...
then run your sproc on a timer under jobs, set to run however often you want it...
you will need smtp sendmail set to run on your sql server, i ran into this problem before
off the top of my head i can't remember the coding, but its something to possible search on
i'll try and look up some of the job sprocs i've done...
daveJam
even my shrink says its all your f#@/ing fault