Amazing write up thank you. If you haven’t already tried you may enjoy the how other dad’s dad podcast by Hamish Blake. It definitely has some things in it which may change your perspective.
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I am in horizontal construction (in Australia) and it is pretty much the same story. The key is having a person who can relate to both the corporate & project people, and has the understanding to translate that into a useful product. Quite rare it seems.
I can second this method, I use docker to generate my frozen requirements though. This allows you to get a frozen set of requirements from a clean environment without the random stuff that can be installed locally.
I have been really impressed by the quality of the releases lately. It has been interesting watching the changes after Tom Christie managed to become full time on it [0] (and the successful Kickstarter campaign [1]).
I would love to see this sort of funding become more common place.
I was using rancher, but it is seriously memory hungry (mine seemed to need 2G) so you would need a $20 Digital Ocean box just to run rancher. Also, the agents / monitoring rancher uses was eating quite a lot of memory / CPU on each host.
The new version of drone (0.5) is much better imho, although it is still in beta so can be a bit frustrating at times. They have relaxed a bunch of the constraints and removed alot of the magic. Plus plugins are alot easier to write now.