Whether it's a pain or not depends on how you have the domains setup. If you use Digital Ocean and Dreamhost for your DNS, it won't be a problem at all, you jus

Whether it's a pain or not depends on how you have the domains setup. If you use Digital Ocean and Dreamhost for your DNS, it won't be a problem at all, you just transfer and it copies the correct DNS with the transfer. If you are using Godaddy as your DNS as well, then you'd probably first want to transfer the DNS to Dreamhost/Digital Ocean before initiating the transfer.