I think this is how it works: If you upgrade your package you can keep the IP; however, when you upgrade packages the disk space stays the same as what you originally purchased. There is a method to resize your disk space, but you lose your IP when you do that. I have read that DigitalOcean is working on fixing this. I’ve been here for a while and the Company does seem to take seriously what it’s users want – I’ve seen several positive changes. I figure they will get this fixed as well.