Earlier quoted context omitted.
Yes, you'll spend some 2 days setting all services, testing, setting backups and alerts, testing again. Add another day if you want redundancy. And then, every 4 to 8 months you'll spend some 2 hours making sure everything is working right and up to date. If you get into another user-base class (like, from 100 to 1000, or from 1000 to 10000), you will spend all those 3 days again. Compare that with cloud services, wh…
And building on barebones keeps all options open. If you go big and realize an IaaS solution is right, great, you are ready to go on to IaaS with no trouble If you IaaS from the beginning, you've cornered yourself and have to build your way out.
You are not ready to go IaaS with no trouble if you've already built your own. It's just as hard to do that as going from IaaS to your own custom infrastructure!