Thank you for the in-depth reply. Interesting thread to read. Starts with the same comment I made. But yes, I understand these difficulties in balancing, and even releasing a starting image and keep unmanaged could be not so efficient considering the multitude of needs, as you mentioned.
After these last days using, configuring, and playing with my instante I'd say the big thing to invest is not in pre-made images nor intermediate products but documentation indeed. Although as you also mentioned before it is just a computer and everything documented anywhere is valid for DreamCompute as well. And I know you're working on this.
Now speaking of my particular case, I'm not coming back to VPS. These steps I'm taking to learn about server configuration and security are a must anyway, and the flexibility I get is...no words to describe. Configuring my own deployment, installing my Perl modules, latest software, etc.
One last question: how are the plans for a mail server going? This is apparently the only thing I'll miss after leaving VPS. Bigger projects/clients prefer to use Google Apps anyway, but the small projects requiring mail only always used DreamHost mail servers and it has always been a success.
I'll maybe try some other services like Zoho, but certainly having a mail only service from DreamHost (which I trust) at a reasonable price would make me happier.