While there's a lot of improvement that can be made here, any changes will be slow to adopt. I think you're ideas are great and echo a lot of what has been discussed in the past. The occasional image loading failures were due to an aging 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.