No I meant 993, technically that's an IMAP port tho, not POP3
Actually I have an outlook.com account and just went and played with it (sorry I was short on time earlier).
There is an auto-configure, and it works, but it doesn't auto-configure for SSL. To use it just type the email address and password without touching the "Advanced options" link, and it will find the dreamhost mail server and configure correctly but without SSL.
Once I got that working, I started editing and found that if I use the alternate server address (which bypasses the certificate issue) mail still connects. So then I switched to ports 995 for POP and 587 and checked the SSL boxes, retested, and it worked.
The ONLY differences from what you typed and what I did are:
-- I'm on a different dreamhost mail cluster than you so I used a different alt address. Those addresses can be found here: http://wiki.dreamhost.com/Certificate_Domain_Mismatch_Error
-- I used baby steps: autoconfigued, tested, then changed the servername and tested again, then changed ports and added the SSL check-box and retested.
If you're still having trouble, one relevant test that you should make if you can is to configure outlook (the client) or TB using POP3, sub3.homie.mail.dreamhost.com, SSL and 995/587 and see if THAT works. If it won't there, then there could be a problem with sub3.homie.mail.dreamhost.com that doesn't exist on my mail cluster.