We love Middleman for static sites; curious why you chose to go with a server instead of S3+Cloudfront or Netlify. One of the biggest reasons we use static site generators is the ability to CDN the whole thing, making it dirt cheap and blazing fast.
I've actually used Netlify numerous times and love it. The simple answer to why I chose to manage my own server was mostly to learn how and have full control.
For what you get out of the box with this setup (or Google Cloud Storage + Cloud Load Balancing/CDN) it actually can be "dirt cheap", depending on your business goals/traffic. Just like anything, it depends on what you value/what your time is worth. The pricing difference would need to be several (several) orders of magnitude larger than it is for me to worry about the few dollars a month I'm spending on each static site sitting in S3/Cloud Storage.
Also, if there is an issue with either of these it's far easier for me to justify downtime to a client by saying "Amazon us-east is down, here's Amazon's status page" then trying to explain who OVH is.
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 :)
In addition to https://www.oppslist.com (as some have already mentioned), check out https://www.indiehackers.com. Although not all the businesses are entirely passive per se, there are a lot of interesting stories and projects that you might find inspiring.
Nice work, how long did it take you to build? Just a note — the pause/play sequence resets the track to the beginning instead of starting it from where you paused (chrome 41.0.2272.76 (64-bit))
Thanks! Started this originally back in the fall of last year some time. Completely threw away all the front end code of that and picked up the project again maybe ~1.5 months ago? Been mostly weekends and some weekday nights. And thanks for reporting the issue, I'll look into it.