I ran many VNs on my dual boot Arch/Gentoo box before installing 7 so I have some experience I can share. All of them were translated.
Insani releases native Linux versions of almost all their translations. Narcissu 2 is like this too IIRC. You can actually use the statically linked Linux executable of (P)ONScripter to run any (P)O/NScript game such as Tsukihime, Tsukihime PLUS+DISC, Kagetsu Tohya and Ballad of an Evening butterfly (saves will be dot files on your home folder, tipically .gamename for ONScript games and .randomcharacters for NScript games). Download it at http://onscripter.unclemion.com/releases/ (if unsure get http://onscripter.unclemion.com/pub/onscr/onscripter-en-linux-i386-20110413.tar.bz2 unpack it and copy onscripter-en to the game folder and run said executable).
Kirikiri games such as Fate/Stay Night tend to run fine through wine as the engine itself is open-source, although some proprietary extensions (such as some F/SN effects) can bring trouble. Just save often, ctrl through the problematic effects and backlog it. I got this problem about four times and I got all endings (plus tiger dojos) so it's perfectly playable.
Nitro+ games are weird. Saya ran fine through wine but with a few random crashes. Kikokugai refused to run most of the time, but when it did I completed the game experiencing no further trouble. Chaos;Head patched fine (the bat didn't work, I just did everything manually) but the game itself didn't work (main menu had no buttons at all).
Ever17 simply didn't run. SWAN SONG ran fine under wine, though it was annoyingly slow during effects (such as the earthquake near the start). Sharin no Kuni worked like a charm with wine, as did Planetarian. Inganock, Wanko to Kurasou and Utawarerumono are three games that I can't remember where I played. IIRC, Utawarerumono ran fine with wine, Inganock and Wanko failed.
That's pretty much all I can say. Do note that this was done with old versions of wine, so your mileage may vary. Oh, and I used the native cdemu to emul
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