Earlier quoted context omitted.
A VPS costs 5 bucks on DO and I've seen (can't remember where) a 3 USD/month offering. So it's rather cheap to move away from shared hosting nowadays. For me Let's Encrypt came out at the right time. They said they will automate the 90-day renewal process.
Side question, does anyone actually enjoy running a VPS? Between managing the sites on it, you have to maintain the VPS, keep it up to date, its prone to security bugs and flaws, etc. Am I missing something here? I remember setting up multiple VPSes on Linode / DO and it was always a painful process of installing the OS, installing the whole stack, configuring everything, setting up users / roles, firewalls, etc. On…