You will need to spend time to set up your site for Amazon or for cheap DO instance, I don't see what you can save here. You can have your own virtual server with root privileges and iptables and custom software and with Amazon you will have to pay for every new feature.
As I said, it really just comes down to business goals. Setting up a shared DO box with iptables isnt worth my time when it's still just a single DO box at the end of the day.
S3 + Cloudfront + ad hoc Lambdas is a far far easier cost benefit ratio when it comes out what my time is worth. To each their own :)
Ha. Well, it's more that there are things I can justify charging for and things I cannot. Standing up a sub par solution for a larger investment of time doesn't make a ton of fiscal sense to myself or my clients.
Yeah indeed, for contract customers, better go with something you're confident everybody will already know, since other people will have to manage it when you won't be there anymore.
In a previous startup I was CTO and founder for, I used a gentoo and managed everything possible by myself. This was not especially costly in time because I was already used to it and efficient, and we managed that way to stay for 3 years with 70€/mo in infrastructure cost. This has its advantages too :)
