The agency I'm currently using seems to be finding it difficult (or lacks the desire?) to implement a contact strategy. We are left to using spreadsheets,
plotting when emails are going out -- and to whom -- and estimating how many times we could be contacting one person on our database. Shouldn't it be straightforward to review email addresses and
calculate the number of times that a person has been contacted -- and, from that information, delve deeper into their behavior?
The answer to your direct question is, yes, your email application or external database should allow you to determine how many times a person has been contacted and delve deeper into their behavior. These tools, however, can't do the thinking and planning for you. It is difficult, and a humble spreadsheet can be useful for keeping track of timing and likely scenarios.
You need to have the big picture: who, what and when. If your program is so complex that it's impossible to keep track of the iterations, you need to have business rules in place that manage it for you, e.g., "do not mail if the recipient has received more than one email per week for four weeks, excluding transactional messages." But again, it's you that needs to understand what the system needs to do to execute your strategy.
That said, you may be suffering from a data deficiency. The Email Diva has used and demo'd many email applications, and not all aggregate activity at the user level. They can analyze and compare campaigns in a million different ways, but many don't keep track of emails sent, opened, clicked, etc. by a user. Those that do, however, are not just the high-end systems; I've seen bargain tools that have it and high-end apps that don't.
If your email application doesn't haven't this functionality, you may want to download your email data to an external database, which may also contain purchase, profile, survey and Web activity at the user level. When building this complex database, follow Elaine O'Gorman of SilverPop's advice: start small. I have seen companies get so tied up with trying to include everything they could ever need that a) the project takes years to complete and b) there is so much data that mere mortals can't make sense of it.
Your database design should flow from your larger strategy. Define your business goals as well as the desired audience experience, then quantify the data needed to execute your strategy. Start with the "must have," and add the "nice to have" later.
Beware of problems caused by a misalignment of the business rules between the two systems. Make sure you're not losing subscribers: compare the list pulled from the database with the list imported into the email app. If there is a large discrepancy, put your IT folks to work until they fix the problem.
Wishing you actionable data and...
The Email Diva