While there's a lot of improvement that can be made here, any changes will be slow to adopt. I think you'reyour ideas are great and echo a lot of what has been discussed in the past. The occasional image loading failures were due to an agingageing server which is running the hostmar.co domain. It's been migrated, and pending DNS, will be resolved in the next 48 hours.
Furthermore, I'll make sure the rest of the moderation team has access to this machine to help manage logs and any errors that might occur going forward.
From what I recall several years ago it was more than just a simple find replace, the Stack Exchange team detailed what seemed to be quite a bit of work to replace every entry of X and was only reserved for drastic measures. That's where the hostmar.co
alternative came from. It happened to be a domain I had at the time.
We can, in addition to your suggestions, also consider just building out what runs hostmar.co
(which is now just a set of NGiNX rules - was a php script). Giving us the same capabilities but with a more crisp domain name.