I have two rails SaaS apps that generate increasingly fulltime income on heroku.

combined costs currently at $140/month each app has 1 free web dyno, 1 worker, starter postgres DB, ssl, plus a few extras

Looking at the new offerings like digital ocean, i'm really tempted to switch over, but a voice in my head keeps telling me it makes no sense as I don't really have strong linux-sysadmin type skills. Even getting rails to work on new macs takes me 1-2 painful days.

Anyone have an eta of what it might take someone with limited sysadmin skills to cut over to something like digital ocean from heroku?