Hi,
This is best done with OOTB workflow and batch process of some sort. It is not a good idea to have a waiting workflow for 30 days duration. If it was any of my clients I would suggest use workflow to send emails. Check the rest of
the conditions in batch process (SSIS / .Net application) which runs on daily basis and performs rest of the checking. Also would suggest storing the configurations in a configurations of some sort entity / XML file.
Hope this helps.
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Minal Dahiya
blog : http://minaldahiya.blogspot.com.au/
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