I don't get the same feel from
Chester as I do from
Weldon and Hilton. With
Weldon and Hilton your description of clunky, old-fashioned and nerdy fits just right. But
Chester feels more awkward and misfit-like to me. Like the difference between intelligent-nerdy and awkward-geeky. Anyhow, I think Hilton is neat.
Weldon is alright too. I like it more after your weldin' association. :) And I don't think it sounds too much like well-done at all.
Hayward and
Maynard came up when I nymblered (I like that you verbified it!)
Weldon and Hilton. Now there's clunky and nerdy for you!