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But then again, one person is enough to report you as a spammer?
Yes. Not everyone is going to remember signing up or e-mailing you. Some will remember and won't be happy getting an unsolicited e-mail. I know I'm not thrilled when I get an e-mail claiming that I signed up for something, when I know I haven't, or more offers to buy something from someone from whom I bought one item a year ago. Even well-known e-commerce sites send this even if you unclick the boxes that say "Please send me future offers."
I check my spam filters regularly and you'd be surprised who's in there.
From a moral standpoint - I would probaly consider it SPAM unless they specifically requested it.
From a business standpoint - check with your ISP and Hosting Provider. If they consider ot SPAM, you can get your web site and or home/office offline from a single complaint.
If you didn't give the customers an opportunity to opt in at the time then it is too late. If you have a legit reason to contact previous customers individually then slip an opt-in offer into the signature.
The only legit reason I can think of for sending unsolicited bulk email is to offer some sort of warning (e.g. there's a bug in version 3.2 of GeeWhizz, please upgrade to 3.2.1) however, emails of this sort are sent out regularly and most, if not all, are fakes so even this reason is dubious.
Don't worry about the law as much as about your upstream providers. Your webhost, datacenter and ISP are all likely to take a very hard line against even a single complaint. In most cases your webhost will deactivate your site first and ask questions later - because if they don't - they could have their whole operation suspended by the datacenter who forwarded them the complaint.
Legalities aside, this is a little closer to the spam line than I'd care to be with a list of 5000. I know two people who are at this moment considering the exact same thing you're thinking of; however, one of these folks has a list of just 40 (yes, forty) and the other might possibly have 200. And they both know their audiences exceptionally well.
I'd say you need to make sure of your legal ground first, then see if the potential risk is worth the potential benefit. Out of 5000, you will certainly have some upset (possibly irate) people. But if you're really sure 95% will appreciate being included, well, that's your decision! :)
As a customer, I would probably not consider this spam, but I also would probably not click the link to subscribe unless I really felt a need for your services and was confident you'd be providing information I could really use. I do admire that you're offering people the chance to opt-in to receive future mailings. A lot of people in your situation would just set up the list and make people unsubscribe.
So if someone like say Amazon, or e-bay, were to send ten million emails out to their previous customers that would be mass spam of an unimaginable size?
It would be normal business communication.
If this is to people who are already your customers then it is probably not spam.
I have a list of 1500 people who double opted in to get my newsletter (which I pretty much never send out because I am so disorganized), but even so, I would not send them anything EXCEPT the newsletter. They didn't sign up for anything else, and it isn't fair, IMO, to go ahead and send them something they didn't ask for just because they wanted to get my newsletter.
I don't even like it when Amazon sends me spam, and I buy tons of books from them.
I have a new mailing list and I need to import all my old list and the email system will not allow imports because of spam issues, whatever
so what I did is sent and email out saying you will receive this once and if you would like to continue to receive updates please re subscribe here... etc
What I am going to offer them, I expect 95% of them will be happy that they came across this email?
If people registered in some way and agreed to be contacted, you're home free. Otherwise it's spam. Also, sending you a personal email does not constitute signing up for a newsletter.
In any case you should be less concerned about the "legalities" and more concerned about the practical consequences. You shouldn't be worried about the state prosecutor going after you, you should be worried about what action your ISP or your sponsors/partners might take if they start getting spam reports.