Hmm, I was willing to buy Da Capo II and more or less got DCIF as a present from my brother since he asked me about what I'd want. I think anything of about an eight or up out of ten on a personal quality scale I'd be willing to buy. So I'd buy Utawarerumono, but Canvas2 would be a waste of money to me.
Though there's a real lack of officially translated stuff in the first place.
Spoony Bard
Regarding Da Capo 2... the blog Calamitous Intent and some person on the Sakurahana forums were both fairly positive about Da Capo 2. And its average on the Visual Novel Database is good. So if you enjoy boy x girls harem games with slice of life, cuteness, some magical realism, and a modest amount of consensual sex scenes, then it's not a bad purchase.
I'm pretty sure I said that I'd be looking for some rarities at the Hendane booth while at Anime Central. Got there as early as humanly possible on Friday morning, but didn't see anything which was especially compelling. I took a pass on Demonbane, and instead bought the limited physical disc release of the translated version of the original Da Capo. It cost more than just paying Mangagamer for a download, but now I can share it with friends at my club. And it included a character/world guide and a soundtrack.
Just a few days left until my local fan convention, Anime Central. The company Hendane will return to the dealers room. I will be at their booth as early as possible to see what they have. The Windows version of Galaxy Angel is a high priority, since only that version was fan translated. Might consider buying a few other visual novels or romance games while I'm at the con.
I've bought a couple Mangagamer titles in the last year, some translated games on DLSite, a few iOS visual novels, and a few translated console games. Haven't been interested in recent Jast games. And it's been quite a while since I imported anything... it's tough to justify paying for a game until I have a translation patch, and even once I have a patch, it usually takes effort to set it up. To be honest, most of what I'm purchasing these days are independent games written in English.
I'm not sure what my fellow English speaking fans are willing to purchase. Visual novel fandom is still small, and squeezed between the larger fandoms of anime/manga and general video games. We have to fight for just about every professional and fan translation. It's depressing to hear examples of major projects which get very few sales. And works written in English are slowly emerging from the "no budget at all" cellar. That said, I was fascinated when Celso Riva from the Winter Wolves group said the following on Twitter: "[W]hen people ask 'why there are so many girly VN/Dating sim games?' the reply is 'because they buy them instead of getting a pirate copy'" (May 7 2011)
So what about you? What visual novels and romance games are you willing to buy?