ludo never clearly lost in a duel to naga, however if their scrap wouldn't have been interrupted by marka, i'd have to say naga would win eventually.
ludo kind of reminds me of marka ragnos in terms of what he wanted to do with the sith empire, and not expanding it into republic space just yet. smart and devious, but, not smart enough when it came to naga....
i, however, think that ludo can defeat freedon, he had many "role models" to learn from.... or at least to see what can truly be accomplished by the darkside, he witnessed this himself more so than freedon.