That's the point, I've been running servers for 10 years with iptables and apt-get knowledge. There is no "ten years of experience running your own server."
My hypothesis is that everything interesting that happens to servers is not covered by Heroku.
If that were the case, Heroku wouldn't be able to charge for what they provide, and everyone with more than just a trivial app would run their own server.
I think you underestimate what it takes to run your own infrastructure. I'm not saying it's black-magic hard, but it does require a not-insignificant skill set for all but the simplest of setups.
I might underestimate what it takes to run a server, and what Heroku brings to the table, I'll grant you that.
Taking another of my hats, the CTO of a million-user business hat, I still don't know what TCO wise the cloud/Heroku brings to the table. I know about the fast scale up and scale down benefits, no 12 months contract, OPEX vs. CAPEX etc. but have not found any TCO cost calculation based on real tasks people need to do on rented servers vs. cloud.
My hypothesis is that everything interesting that happens to servers is not covered by Heroku.