Thinking of buying a guitar? Learn from my mistakes and misunderstandings.

When I got my first good-paying job, then finally having a little disposable income in my pocket, I deided to buy a really good guitar -- a great sounding instrument that would also appreciate or at least hold its value over time.

Long story short: I ended up buying a pretty expensive guitar (and later selling it at a significant loss) -- a c.1976 Martin D-28. I had imagined that as my playing skill got better, I would "grow into" the instrument.  I confused quality with playability and did not realize that guitars come from the factory set to differing playing specifications, which determine playing characteristics, and I did not understand that playability can be adjusted. 

So unfortunately, this particular instrument had action that was playable, but was set a little high so as to maximize guitar volume -- especially for bluegrass and country players who tended to play open chords down near the nut. I could have paid to have the action lowered, but I wasn't aware of this option.

Or.... I could have bought a less expensive guitar, and paid to have that set up to meet my needs. THAT would have been the smarter way to go.

Here are a few additional lessons from my old, sad story:
Guitars purchased new today are likely to depreciate significantly -- even really good ones. The vintage Gibsons and Martins, which are selling for ridiculous prices today, are mostly high valued because a) they can sound really good, and b) they were produced in relatively small numbers and even fewer survived the ravages of time. Sure they have dried out, which makes for great tone, and some were (too) lightly braced, which also makes for great tone, but also reduces their toughness and durability over time.
Because playability can be set (adjusted) on most guitars of even moderate quality, if your guitar doesn't play to your liking, consult an expert luthier (builder/repair technician) and pay to have it improved. You don't need to replace the instrument.
Most instruments (those with a neck made of wood) -- even electric or those those acoustics made from laminate wood (plywood) or of synthetic material in the body -- should probably be stored in a humidity-controlled environment. Any guitar with a wood neck may eventually dry out if stored long term in a dry environment. This can cause the wood in the neck to shrink slightly causing the frets to become relatively longer. This so-called "fret sprout" can be uncomfortable on your fretting hand, or, in some cases, can damage binding on the neck. Therefore even solid-body guitars should be humidified in dry climates or during the heating season. In acoustic guitars that have a solid woods (not laminate) for the entire body or just the top of the body, these are prone to cracking and other physical damage if not stored in appropriate humidity. Changes in humidity can also affect playability as the action raises or lowers due to humidity changes. 
When storing your guitar long term, always de-tune it to lower the string tension. The longer the storage, the lower the tension.

After I bought and eventually sold that D-28, I cycled through various guitars including an Ibanez 12-string acoustic, a Harmony arch-top electric (a very poor man's Gibson 335 imitation), and an Ovation legend acoustic electric.  About 20 years ago, after selling all my other guitars, I bought a new Taylor 412-ce and have had that ever since. I bought the Taylor guitar for several reasons, but among them was the fact that Taylors are known for their from-the-factory playability. They tend to have low action, which is great for players that play over the entire finger board, as well as being great for relative beginners. (At the time of this purchase, I still didn't know that action was adjustable. So for a second time, I ended up paying way more than necessary to get an instrument that met my needs.)

However, with the advent of the Internet and YouTube, I had started watching guitar-repair videos. From these I learned how guitar set-ups are done. 

Then I acquired a kit for a semi-hollow-body Telecaster-style electric guitar. I acquired some specialized tools for guitar set ups and also used the knowledge acquired from the many luthier videos that I watched. 

Then finally, using the tools and experience from building the thinline Tele-style electric, I bought an all-laminate cutaway acoustic from Orangewood. Though not well set up upon arrival (despite their claims to the contrary and those of customers who don't know a lot about proper guitar set up), I did my own custom set up and repairs as necessary to make this instrument -- the least expensive guitar I've ever owned --  one of the most pleasurable to play. Even its voice is pretty darned good. This guitar cost $135. My Taylor would today cost $2400. No disrespect to the Taylor, but the Oragewood, even with its many imperfections out of the box that I corrected (with a retail value of about $100 because the $135 price included a case and shipping costs), was the much better value. If I had it to do over, I'd just have two guitars today: my thinline electric and my Orangewood Rey Mahogany.

So the bottom line is this, all guitars have their own voice -- the enjoyment of which is a matter of personal taste. Expensive guitars usually have expensive materials and often fancy decorative appointments. You pay big bucks for materials and flash. Yeah, their tone may be different, and what some would say is superior; but how much better? Is a slight difference in tone worth $2000? (I don't think so for most players -- especially student guitarists.) A good playing guitar can usually be made from most instruments above toy grade, but if you're not sure, consult with a set-up expert before you purchase. An $250 guitar ($135 initial investment plus not more that $115 in adjustment/repair costs) may not sound exactly like a $2500 guitar, but paying ten times more won't buy you ten times better sound. Virtually guaranteed.