That's not a problem specific to lets encrypt, or anything else really.
If you don't want to introduce complexity, then your problem is that you don't have tooling in place when you run into a situation where you have to rotate certs.
You can see the full log of errors with diagnostics from the 'Results Log' menu item. You're right, there should be a link to the log from the dashboard items.
That would work for a percentage of bots. That method is used in the ad fraud detection world, but a lot of the bots simulate mouse moves and other user activities now. There are other ways to whitelist visitors, however.
We develop in Windows and Mac and they have been remarkably solid with a few gotchas.
One, the case sensitivity of file names.
Two, compiled modules have not behaved well on Windows in all cases. We tend to avoid them.
Three, the path length has definitely caught us. However, NPM now mitigates that with a new flatter directory structure.
ERP and mindfulness are really, really effective in treating OCD. I know, because one of my children had a crippling case and now is free of it. I spent several months at UCLA's Pediatric Intensive Outpatient Program with him and have seen it work on about a dozen children. The same treatment can also be used on adults.
ERP stands for Exposure and Response Prevention. The idea is that you progressively expose the person with OCD to their fear(s), during which, they cannot perform any compulsions. Eventually the brain is retrained and the OCD falls away. For example, someone with a fear of germs would be asked to touch a door handle and then not wash their hands for as long as possible. This is extremely hard for them. However, this simple technique, applied over weeks or months in conjunction with therapy and meds, can reduce a person's OCD to almost nothing.
Another point is that the kids respond to the group setting. They form bonds and support each other during the process.
It's kind of like ebay feedback. Not perfect - community driven. I think the geolocation can prevent fraud, but it can be gotten around. It is just an informational tool.
I've paused in fear many times before hitting Send on a Bitcoin transfer. I would use this for slightly more ease-of-mind.