I find it depends what you want to do with those sites. If they are for a client, then they can have their own VPS as makes billing clear and easy. With team development I have maybe 6 Joomla/WP/Laravel sites on a $5 DO server. With Swop reasonable size it works fine when such low traffic. Issue we his was available ram. With 3 reasonable size sites MySQL maxed out ram and strange things started happening. So depends more on your DB and memory demands and that is also influenced by traffic.

When you are often on the road or speaking, how long in advance do you plan work for you and the team on projects? (or do you give that task to someone else)

Do you find jsbin a work of love or do you like to have projects like it to bounce between client work?