Similar story over here. I started by offering shared hosting with supervision as added value, expanded into reselling VPS'es and eventually leased bare metal servers that I partitioned into VPS'es. I could have made a lot more money if I didn't treat every customer with utmost care and attention. Now I'm stuck with clients that can't afford to go elsewhere and clients with grossly outdated software that would be a nightmare to migrate. I kinda miss the passive income although there wasn't much. On average I had to fix something every few months and would get a major outage/bug once per year. I always hesitated that scaling up would result in more customer support work, more major outages and more everything that would take the "passive" out of passive income.
Sounds familiar! I really did enjoy the work and helping people, but I could never find anyone to help me, and it's a 24/7 thing. I have basically never been offline since 2002. There's been a few exceptions, but I'm always on call. It's been a good ride, and I know I'll be sad when I cancel that last server next month. Let me know if you need help, I'm available now :-)
