I think Drow and Poiumty pretty much covered a wide variety of good potential starters. I went with "A Drug that makes you Dream" (Yume Miru Kusuri) as my initiation into the genre, after reading the user review on it, and I would certainly recommend it.
RedEyesBlackGamer said:
Will they run on Windows 7? I see all the way to Vista.
I've actually
just upgraded from Vista to Windows 7, and all my visual novels works just fine. As mentioned, you'll still have to use AppLocale [http://www.microsoft.com/downloads/en/details.aspx?FamilyID=8c4e8e0d-45d1-4d9b-b7c0-8430c1ac89ab] for those few which require it, but it installing it is 3 clicks, and using it as easy as opening it and browsing to the program you wish to start with it.
Be sure to generally put them in compatibility mode for Windows XP though (right-click the .exe file, choose properties, then compatibility), as there can be various technical hickups with older Visual novels on later systems.
When you install a VN that requires AppLocale, you'll sometimes have to temporarily switch your system region to Japanese during the installation (this doesn't change the system language). A guide can be found here [http://blog.wentoday.com/?p=346].
...and that should about cover any technical OS issue you might have to face to get them to run. Bear in mind that the AppLocale and system region change during install isn't necessary for the vast majority of Visual Novels translated into English (I've encountered 2 so far), so generally putting them in XP compatibility mode is all it takes.