I moved to a $5 DigitalOcean droplet running Dokku (dokku.com).

To answer your questions:

1) 2 hours for 8 apps — most work was setup of new DNS and testing

2) I have very litte experience in DevOps

3) I think its totally worth it for the additional flexibility and the super cheap cost

4) Just $5 - can’t beat that

5) 8 Ruby Sinatra sites w/ a total of 20k hits/month