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I'm going to preface this post with the following disclaimer: These are the instructions I give to everyone who asks me, "What gun should I get?" It assumes that the buyer knows little about firearms. If that is not the case for you, please do not be insulted, but take the points for what they are worth.
Guns are like shoes. You need to consider the same things when buying a gun as when you buy shoes:
1. What will I be using it for?
2. What functionality should it have?
3. Is it comfortable?
4. Does it work well (reliability)?
5. Do I like the way it looks?
So, 1, what are you using it for? If self-defense, most guns out there are fine for everyday carry (as seen by the huge variety of guns actually carried by people).
2. What functionality should it have? Well, how many rounds would you like to have? What caliber would you prefer? Can you manipulate the slide or potential jams of a semi-auto or should you stick to a simpler design such as the revolver?
3. When you go to the gun store, have a list of requirement. I.E. I want a semi-auto in 9mm that holds at least 13 rounds. They can then let you hold all the guns that fit that requirement. If they are grumpy about doing so, go elsewhere. Narrow your search down to a few that you like the feel of most (be careful to check the gun for loaded status when they hand it to you and also don't point the muzzle at anyone - best take aim at the ceiling or floor).
4. Does it work well? Well, all guns have to work, at least some of the time. Some guns don't like certain types of ammo (semi-wad cutters, hollow points, etc) and will only feed round nose FMJ or the Glaser Safety Slugs. This is an issue for me on a self-defense gun. If you're only ever going to shoot this gun at the range, then a finicky gun is fine, but I want my self-defense guns to eat anything and everything and function flawlessly. I don't plan on dragging my firearms through sand, dirt, mud, sub-freezing temperatures, etc. so I don't go around saying everyone needs to carry a GLOCK or Springfield XD. However, these guns are engineered very well and CAN be tortured and still function. That kind of reliability says a lot in my opinion and makes me very comfortable with carrying those two brands.
5. Do I like the way it looks? While not essential, it is important. This is something that you will be looking at every day. If you OC, it will essentially become part of your wardrobe. If I were going to drop $500 on something that I wore around every day, you had better bet I would like the way it looks. I'm pretty easy going in this category, there are very few guns that I dislike the look of, so let's pick the numero uno ugly gun: Desert Eagle. This gun is enormous and can be found in the ever so ugly gold-plated edition. To me this gun screams "I'm compensating..." you know the rest. The cartridges it fires are the .357 Mag, .44 Mag and .50 A&E. Seriously, .50 caliber? Psh...
Anyways, after you have held a lot of guns and found the ones that fit your criteria, are comfortable and you like the looks of, go shoot them at a range (rentals mentioned above). You will soon narrow your selection down to one or two guns that you like the best. After that, it's simply a matter of shopping around to find the best price. Just call up all the gun stores and have a look on KSL. New is nice because you know that it has not been abused. As you get more familiar with guns, you may want to venture into the used market as you will know what to look for and how to recognize a gun that's in good shape.
Best of luck, please let us know if you need more help or advice. Also, please let us know what you settled on (and that means pics!!!).