Mass Emailing Contacts beyond the Outlook Contact Groups limitations

We have a user that is currently using Outlook 2010 and we use a Hosted Exchange 2010 platform for our baseline.  This user has built up a list of contacts into groups in Outlook.  This user sends emails to these contacts on a daily basis always using BCC to keep the recipients discreet while getting bids for a current project.  This has been working well for months for this user but the Outlook Contact Groups are getting to a point where they are starting to fuss about the size.  The contacts have a bit of details inside of them like the signatures pasted in (pictures included) and details copied into the appropriate fields so they are not so tiny anymore.

My question has to do with trying to find a better way to send emails to these large lists of people.  Keeping the contacts inside of Outlook isn't the problem but more the problem concerns the number of contacts inside of a Group.  He has some Groups and we talked about breaking them out alphabetically and creating multiples next to each other but that would get less organized and confusing overall.  I thought about using software like Infacta's GroupMail which acts as a mailer but I don't know if this would simplify the grouping of contacts any better.  I also thought about using Constant Contact (with Outlook Sync options) but that isn't really the strong point for CC either.  I am looking for some software that can synchronize up with an Outlook Address Book (Contacts) and make it easier to send emails to a bunch of users without having all the limitations of the Outlook Contacts' version of Groups which appears to be a smaller scale version of what we need.

Any thoughts are welcome.  Thanks.
alatham23Asked:
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Alexei KuznetsovMicrosoft Outlook MVPCommented:
First. You can group contacts by folders. Just create subfolder of "Contacts" type and move the required contacts there. Also set the name of the Outlook Address Book for this folder in its properties. Now you'll be able to select contacts from this folder.
Second. You can safely ignore "This distribution list contains more members than supported ..." warning if you do not plan to use pre-Outlook 2007SP1 with your contact groups: http://support.microsoft.com/kb/238569
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Helen FeddemaCommented:
Using VBA code, you could send emails to all contacts in a folder (as in the previous post), or select contacts by category.
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Mark GalvinManaging Director / Principal ConsultantCommented:
What about using something like www.mailchimp.com? I use it for marketing emails but it could be used for the task your client needs. And depending on the size of the lis it might be free.
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alatham23Author Commented:
thims
First. You can group contacts by folders. Just create subfolder of "Contacts" type and move the required contacts there. Also set the name of the Outlook Address Book for this folder in its properties. Now you'll be able to select contacts from this folder.
Second. You can safely ignore "This distribution list contains more members than supported ..." warning if you do not plan to use pre-Outlook 2007SP1 with your contact groups: http://support.microsoft.com/kb/238569
I have dealt with different Contact Lists before and may need to go a different direction like that potentially.  The problem is, there are close to 10 different groups so that would be quite a few separate Contact Lists.  We have been ignoring the 2007 warnings but just wanted to know why the limitations when using Outlook 2010 but it may be an older Contact Group that was created in 2007 perhaps.

Helen_Feddema
Using VBA code, you could send emails to all contacts in a folder (as in the previous post), or select contacts by category.
We could use VBA code but I don't want to add programming to the situation for this user.  Also, the categories are being used but in a different way so that would not be an option for this time.

Mark Galvin
What about using something like www.mailchimp.com? I use it for marketing emails but it could be used for the task your client needs. And depending on the size of the lis it might be free.
The list would be below the 2000 subscribers and 12,000 emails so it should be free.  I will see if this would be a way to go.  I was more looking at a way to integrate into Outlook with a plug-in or something but this may be another option.
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Mark GalvinManaging Director / Principal ConsultantCommented:
With mailchimp not only can you send the emails with the recpients name/email being in the To field (more personal) - just like a proper mailer, all replies go to a nomitated email address on yoru system. And you get tracking benefits as well as list management tools such as Add My Friend or Unsubcribe me. Also. there is NO CHANCE of your domain getting black listed as they send the emails out in blocks.

I used the free version for a while and it worked perfectly for us. It was only when our lists exceeded 2000 we went for the paid for basis.
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