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I do not have extensive experience with multiple guns, experimenting with multiple calibers and bullet weights. That said, from what I have read, one's chances of finding a "keeper" on the first try may be enhanced by choosing a handgun that fits your hand properly and feels comfortable in a proper firing grip, selecting the caliber that the gun was originally designed around, and shooting the bullet weight (and design?) that the gun and/or cartridge was designed for. This calls for a little research on your part, though forums like this can be helpful.

Just off the top of my head, I would guess that a 5" 1911 design in .45ACP, using 230gr bullets, or a Glock 17 (chambered in 9mm of course) would probably be more reliable choices than a 10mm 4" 1911 in 10mm or 3" 1911 in .45ACP, or a Glock 27 shooting 135gr bullets. It is not my intent to be hating on 10mm or .40 S&W, or compact guns or flyweight bullets; what I am saying is that conservative choices in handgun design, caliber and bullet weight will probably yield the best chance of a winner from the outset, without spending a lot of time and money experimenting. Make and proof your choices in hardware (the method for doing so may be a topic unto itself), then spend your time, resources and effort tweaking your software (your shooting skills) and you will be more capable of handling whatever challenge you may face in competition or the street than if you spent your time constantly tweaking and experimenting with different bullets and guns.