I shouldn't have to worry about these things if all I want to do is make a quick goofy little icon or whatever.
Does Paint even include an exporter for an icon file that includes multiple sizes?
But sometimes, part of the job includes knowing when to pick your battles.
True. I'm also aware that which battles to pick depends on how expendable the company considers you to be. This is probably why I haven't had quite as much problem getting GIMP approved as some other users are reporting, as I've worked at mostly small businesses.
This brings me to another point: Sometimes, picking your battles includes picking your employer. "I left when I realized the company made a habit of refusing to provide suitable tools to do my job on a reasonable time frame. Assigning projects that require image editing without allowing use of a basic image editor, even one distributed as free software, was the last straw."