I'd start with Taylor, which are the best quality "off-the-rack" acoustics on the market, IN MY OPINION. They also do custom work, but I generally don't compare them against custom luthiers. I own three Taylors, and am rather serious about my music. If you buy something really cheap, chances are that you won't play very long, and will be stuck with a good candidate for your next garage sale.
Taylor offers an entry-level Baby Taylor, probably for under $300. I've played them, they are easy to play, and sound sweet. If, after playing awhile, you decided this just isn't for you, they'll probably have a fairly good resale value.
I would strongly urge you to start out with a good teacher, just to get you going, avoid bad habits, do things the right way, etc. Believe me, just a few lessons could save you countless hours of struggle, and give you a major kick-start to your guitar playing.
An excellent site that I highly recommend is www.totallyguitars.com. They offer guitar lessons for all levels, from absolute beginner to accomplished player. They have free lessons, packages, pay-as-you-go, and monthly subscriptions. Also, they have very detailed lessons, plus music tablature, for a bunch of songs.
You just have to make a commitment to playing. Period. I know it looks easy, but it isn't. Play every day. Don't hurt yourself. Have fun. Learn all kinds of scales & chords. Concentrate on a few songs that you really like, starting with the easiest. That will keep you coming back to the guitar, and will become addictive.
Go to as many guitar shops as possible. Pick up guitars, regardless of price, and try to pick out a few notes on them. Talk to the cats behind the counter. Don't worry, they really do like to talk about guitars! You'll probably run into some guys trying out guitars, as well. Ask them questions. They'll be flattered. Also, they'll tell you about their experiences when they were just starting out. These are invaluable, and free, sources of information.
Good luck with your guitar journey! I played other instruments professionally for many years before I took up guitar. I'm still kicking myself that I didn't start sooner!
Froppe '76