Times New Roman was designed for small newsprint, printed as cheaply as possible on crappy paper. For that it works fairly well. At normal size, though, its schizophrenic design becomes an eyesore.
More importantly, the default Microsoft versions of Times New Roman have shitty kerning, are set not to use ligatures by default, use capitalized (“lining”) numbers, and so forth. If you redid all of the kerning tables by hand, and used a better typographic engine than MS Word, you could get Times New Roman to look passable; it’s never going to be beautiful though.
More importantly, the default Microsoft versions of Times New Roman have shitty kerning, are set not to use ligatures by default, use capitalized (“lining”) numbers, and so forth. If you redid all of the kerning tables by hand, and used a better typographic engine than MS Word, you could get Times New Roman to look passable; it’s never going to be beautiful though.