In general I'm usually too broke to buy a lot of new gear. I splurged on a number of pedals a few years ago when I was setting up my board for the first time but that's really it. I still have the first guitar I ever bought at 17, a Les Paul Studio SmartWood (didn't know that was the model at the time...). I found some pics online, this is basically the exact guitar I bought over ten years ago and still play/perform with regularly. I do love it and its dual humbuckers and I can't bring myself to buy another electric yet.
But I digress, obviously, since you asked about acoustics...
I bought my first acoustic not long after (long story short, I had my father's beautiful old 70's Gibson that I learned to play on for years and now...my brother has it, alas). It was a Seagull Folk, about $450, and it still sounds pretty damn great. I like unfinished wood on my guitars, especially the acoustics, the sound seems to change as the wood ages and oddly a lot of people who play my acoustic really love the way it sounds. Plugged in it's not the same, in my opinion, but the sound is hard to beat otherwise. It looks pretty much like the first image, but the color is much closer to the second:
Anyway, sorry for the images. I can't find anywhere to buy these models anymore so I nabbed these from the intarwebs. I only own these two guitars and I love them a lot.
Seagull is a Canadian company if I'm right but they make all their guitars in North America (if that matters to you...). I've found they seem underrated for the price point and sound quality.
Obviously if you have cash, it's hard to go wrong with a nice Martin or Taylor. If I were to buy another guitar, there was this small-body mahogany Martin acoustic that I saw Dave playing a number of years back that I absolutely fell in love with, and I would buy that if I could. I think it's only like $600-700. It was an awesome guitar.