You had to wait 14 days in total (for both first and second attempt) or 14 days just for the second attempt?
I'm now on my 4th attempt and 6 days have passed with this attempt still pending.
Here's what I did: I disabled the whois and the domain is NOT locked, it's not in the 60 days of pause between transfers and it's nowhere near expiration. I have access to the whois email and checked the spam folder also.
So, I've requested the transfer from NameCheap, entered the EPP key, etc, a few hours later I've received a confirmation mail from Namecheap and approved the transfer.
Can you tell me in detail and step by step how did you manage to transfer the domain? And did you receive any confirmation mail from Dreamhost also or just the one from NameCheap?
The domain was finally transferred just a few hours ago after all this hassle. Here's an advise for those of you who want to transfer their domains and encounter issues.
Dreamhost did NOT send a confirmation mail so do not wait for one or do not resubmit the transfer after a few days. Submit the transfer, approve it through email and wait up to 10-15 days for it to complete.