Doesn't specifically help you I realise, but I can confirm that I also use a custom domain via Outlook.com - with a number of family email addresses set up, using both Outlook 2010 (with Office Outlook Connector) and Outlook 2013 and also Windows Live email. We don't appear to be having any such problems, so it seems it must be something in your particular environment.
Off topic, but I'm more than a little annoyed about Microsoft's announcement that no new users can be added to custom domains after 31 July. I realise that they are attempting to push everyone to a paid Office 365 service and I don't even object to no new custom domains being set up, but the disabling of user admin in existing domains just feels petty.
hashbrown: DNS perhaps? Maybe try hard coding DNS on those machines to bypass modem, or test Google DNS.
I might suspect DNS if it was failing totally, but it seems to be failing based on the size of email inc. attachments. As mentioned earlier, the email usually does send, but only with partial (if any attachments).
For example:
I may send a short text email with 5x 500kb jpgs attached. The email will say it failed, but may in fact have sent, but only 2 of those 5 attachments are sent.
Or, I may send a text email with a 1.5mb PDF attached. Again, it will say it failed, but sometimes the text is received, but not the attachment.
It's working perfectly on the same PCs now using Outlook 2013 connected over EAS. No idea why it wasn't liking the connector you need to use with 2010. Maybe different server addresses it was having issues with over that connection? Who knows.
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