Love paying for things that I don't get. It's been almost a year and a half and no progress on what seems like a simple feature. One of the primary reasons I signed up with Digital Ocean is that I could upgrade my droplet as I needed resources. Meanwhile, I'll be looking for a better host.
I've migrated to www.linode.com . they offer this feature! recommend taking a look for anyone disappointed with Digitaloceans progress and their obvious lack of customer support (You can snapshot your droplet, destroy it, and re-create it so your disk is correctly resized. This way you will get what you are paying for :))
Wow, I actually can't believe the "progress" on this thread. Kind of feel this is one of the most basic "features" for a scalable cloud solution. Haven't looked into linode. Got some free DigitalOcean as part of TechStars, but might have to migrate to linode now.