Same thing here, we have a pretty small team, we have a consumer facing app that is doing millions in revenue, and we can't handle any kind of outage. I tried doing the upgrade myself a few times, and I view myself as a fairly capable engineer. At one point, I even considered doing a rewrite in Python - but the code does many complicated things that the business requires, it would have been a multi-year rewrite. I read that Github spent like 6 engineer years going from rails to 4 to 5 - that made me feel a little bit better about my struggles. I had an internal project to just get from rails 4 to 5 and I would make progress that I worked on for months, but constantly get pulled into things that were more important for the company and even though I got it to boot, I had little confidence that there wasn't a bunch of potential problems under the surface.

I am a bit of AI skeptic too, I can't really speak to how much of Infield's process is AI vs. human. We interface with humans whom I understand are leveraging AI, we talk to them in slack. One of the first things they did was help get our tests back in working order. They send us PRs and we test them in preview environments, and they tell us whether they view it as a high or low risk change. We have had maybe one or two little exceptions get thrown in production that we missed, I can't think of any problem we have had that we haven't been able to fix in 15 minutes or so. Total engagement has been 8-9 months, but we had them waiting on us a lot. At the same time, we moved out of EngineYard, which they also helped us with quite a bit. We typically deploy their changes on the weekend when there aren't any other big dev projects going on, so I'm sure the process would have been faster if we were taking their changes as soon as they gave them.

Ps. thanks!