I think if you're able to write good supportable software, you should be able to write quicky "holy crap what was this guy thinking" software, but if you're able to write the latter, you're not automatically able to write the former.
In other words, hire good programmers, and tell them specifically what you want and how you want it. Think short order cooks - they'll make exactly what you want, but they need to know how you want it.
(The Short Order Cook Law Of Software Design is definitely a book I should write...)