Oh, it's been thought about. I am very well aware that the site looks like something from 1997.
There are a couple of issues, but it's mostly my lack of willingness to put in the time to learn something new (I do have a YouTube channel, other personal projects and things to do), and also my lack of trust to ask someone to do it for me. I realize how really stupid both of those sound, even moreso when I type that out. "If it ain't broke, don't fix it", they say. But I guess while not necessarily broken, the site being more than a little unwieldy and outdated isn't really much better...
I would certainly be open to a system that is easier than the current process, such as one that allows maps to be uploaded easily and with all its info automatically displayed without me having to type in filesizes and image areas, etc., basically anything that would save me a ton of time. The trick is figuring out how to start making changes when there is already so much content.
I do have some real-life friends that know about computer stuff. I could bring up the idea of working on it with them. I've shied away from working with friends in case things go sour, because that's happened before, but I'm probably being paranoid.
I'm open to suggestions. Well, open to hearing/reading them at least, I honestly don't want to promise anything.