Without a doubt, Jason has the best intentions here, but I'm getting a really bad vibe from reading the entire thread -- particularly the by the way, you contributed to a ticket and I can look it up so I'm going to remind you so that you'll look stupid for bitching about us bit.
The hostile you-are-wrong attitude, while maybe technically correct, is a disaster for outside perception.
Textdrive promised lifetime hosting. Where does it say they promised hosting on the same box for that entire lifetime? TxD/Joyent has been gracious to provide hosting on their new platform.
One could argue that the 'lifetime' was referring to the actual box, and if the downtime is increasing, the lifetime of the server is ending.
I say pull the plug and force the migration. Granted, it could be a small PR hit.
You Joyent folks will never get a subset of your customers to migrate off textdrive hardware (so it's no use to keep yelling "just migrate!"). However, if you let those older servers fall apart you'll only get more negative PR.