@Gentlecolt
Well, this year I became quite a fan of Key’s stuff,
particularly Clannad. Of course, that one is pretty expensive, although it’s worth every cent.
Little Busters was recently released, as I mentioned, and some say it’s even better, although so far I prefer Clannad (I haven’t finished LB yet, though).
There’s also Planetarian, which is much cheaper (and much, much shorter), but till pretty good and a great introduction to Key’s games and VNs in general, so I’d recommend this one for the beginning. It’s not as good as their other works, but it shares many of their qualities, so it shows very well what to expect.
Steins;Gate is also very good and pretty well-known, thanks to its anime adaptation (although the VN is naturally better).
Higurashi also has a popular anime, although it can be intimidating, since it’s split into 8 separate releases (not all of which are on Steam yet). And each of them are relatively meaty, even the shortest one could take 10 hours.
It’s successor Umineko has a similar release, but Steam has them collected in two releases (the second one isn’t there yet, but will be soon). It’s even more popular and seen as one of the best VNs in existence. Prior knowledge of Higurashi is not necessary (in fact, it’d make things more confusing).
Other popular VNs, that I haven’t played yet, are
Fruit of Grisaia (although it’s recommended to get it uncensored),
Dies Irae,
Wonderful Everyday (although this one is known to be pretty unusual and very messed up, so probably not quite suited for a “VN Beginner”)
If you have a PS4, Chaos;Child, which was recently released in English and is part of the same series as Steins;Gate, could also be interesting.