Hmmmm if money isn't a problem, then its alright to admit so. Expensive guitars are worth the investment, IF you're sure of what you want, since they're made to last and will only sound better with age. Cheaper (sub-1k) guitars won't mature so well.
There are several things to take note of when looking at acoustic guitars. The choice of wood matters, it defines the tone of the guitar. There are 4 important sections, the top (which accounts for most of the tone), back & sides (lesser), fingerboard (even lesser than before) and the neck (lesser still). Together, the combination of woods will more or less define the tone. You can do more research on woods and their tones at sites like
www.taylorguitars.com (take it with a pinch of salt, they tend to glorify their guitars a little too much, good instruments they are though).
Another consideration is the shape. The shape affects playability (to a certain extent), sound characteristics (slightly different from tone, i'll explain) and the response. A bigger shape (dreadnought, jumbo) tends to encumber smaller people, so do take note. People with bigger bodies (like me, fat) will have no problem with all shapes, except that perhaps a small-bodied guitar might look weird on you (if you're picky about looks). Sound characteristics is basically how the tone is carried forth. Each shape has a different sound characteristics, and each shapes has its strength and weaknesses. For example, a dreadnought, being a boxier and big bodied shape, sounds more full and loud. The jumbo is another example of this. Smaller shapes generally sound softer (due to less wood volume and air volume within the body for resonance) and transparent. Finally, the response defines how well the guitar responds to your picking/plucking/strumming dynamics. Basically, its a gauge of how much the volume/tone changes when you change your picking/plucking/strumming strength or the angle of attack of your pick/fingers. Dreadnoughts are usually less responsive, that's why they're used mostly by strummers or those who want to sound loud and full almost all the time. Jumbos actually have the best response, due to their size and their shape and bracing (another area you might want to look at). Grand Auditoriums are usually the best compromise between size and responsiveness. Generally, you'd want a responsive guitar. More research can also be done online.
Having said all those, a well-built guitar (with a price to match, think upwards of 2k) will be able to give you the best of both worlds (responsiveness and sound characteristics). I've tried dreadnoughts that cost 5k, that were very responsive to my strumming/picking/plucking dynamics and sounded nice and full when strumming, yet clear and transparent when plucking. Tone of course, is more defined by wood than anything else. Its hard to put into words.
That's a whole load of words, yet it barely encapsulates what you need to know. If you're the scientific kind like me, who wants to know every aspect and is willing to expend time and energy researching and narrowing down your parameters before hitting the shops, what i've said should help immensely. If you tire easy of technicalities, then what i suggest is: go straight to the shop, pick up every guitar and try it out. The one that satisfies you the most, grab it. My goal here is not just to suggest guitars ; tastes vary all around. What i'm trying to do is to help you make the choice for yourself. Hopefully with this info, you can make a more informed and thus better choice for yourself. Cheers!
Better guitars at that budget and when you decided to upgrade (which you will), you can resell at a lesser loss.