If I have a couple miners each on a separate worker and then one of them goes offline, does this negatively impact my shares more than if I have all of my devices on the same worker? I had to disable one of my miners for maintenance and I'm concerned that I'm losing more than I might otherwise due to my configuration

From my experience, it makes no difference whether you have 100 workers each with 1 device, or 100 devices all on 1 worker. It should all work out the same at the end of a round.