How long did it take you to find your "go to" everyday concealed carry gun?
My original gun was my "go to" gun since it was my only pistol. I always come back to it. The problem is that it is not concealable with most of my wardrobe.
How many guns did you experiment with before you found your favorite?
I am still looking after 16 years.
I have my best guesses, but that's about it. I compromised and have divided them up into four classes: pocket, small, medium and large. Pocket and small are the most concealable, but lack the capacity, ease of use, and longer sight radius that make the larger guns much better shooters.
I found that a Glock 19 and Glock 26 cover 95% of all situations. The last 5% is solved by a mini semi-automatic pistol or a small revolver. However, I can make do with a Glock 26 even in the last 5%, but it's annoying.
My recommendation is that if you have no idea what to get, buy a Glock 19. Add night sights, grip plug, and a Ghost 3.5# connector. If you do not like the gun after six months, you can always sell it at a small loss (rather than a large one) since they're so popular. But, you'll find that its overall height and width is just about perfect to avoid printing while providing you with a long sight radius and full palm support. A Browning Hi-Power MK III in 9x19mm has similar characteristics (I do not use them at this time due to all the modifications for carry that are needed--figure $400+ in work plus refinishing. ION Bond runs $400 or so). The S&W M&P compacts are a blend of the sizes of the Glock 19 and 26. It may be a the compromise you're looking for.
I have found the SIG P229 to be a good compromise between a medium and large gun. It's slightly larger than a Glock 19. One advantage for shooting is the gun weighs more. This can be a disadvantage as far as your back is concerned. I found it to turn 40 S&W and 357 SIG from annoying to tolerable cartridges. I'd likely carry one in 357 SIG if I could put up with reloading the necked case. 40 DeathRay is just silly (made for those who need a "4" in the caliber), so the obvious choice is hot 9x19mm.
I have found a whole bunch of guns that are annoying or designed by marketing people. Small semi-automatic pistols chambered in 45 ACP are almost universally terrible. They have low capacity and nasty recoil (small 1911's, Glock 36, Springfield XDS, etc). Oversized guns in 380 Automatic are another silly concept. Chambering 40 S&W or 357 SIG in a small semi-automatic is useless, just like chambering 10 mm in very light guns. The shot recovery time is too long and the blast is as bad as full 357 Magnum out of a two inch barrel.
The Ruger SP101 is another terrible design despite its popularity. It's almost as if the design team took all the thrown out requirements from successful designs and munged them together to make this gun. The problems are not obvious. First, it is nearly full sized and only holds five rounds (six is statistically significant for getting two shots into each attacker--see a thread on this forum that goes over the percentages). Secondly, the cylinder crane is not long enough. It is about 1/8" or so too short, which results in speed loaders binding on the rubber grip. Empty cases will catch too. It needs a rear sight rather than a groove and the stainless steel finish makes it tough to line up the sights. Finally, the short barreled version is just too heavy to be a small gun and not heavy enough to be a full sized gun. They should just bring back the Speed Six and Security Six.
Make sure to consider the cost of magazines. HK P30's are great, but the cost of the magazine is incredibly high. SIG has become almost as ridiculous and Glock recently cranked up their prices to $30 or so (wait for sales after the 2012-2013 Panic). Even 1911 magazines are creeping up and high quality mags cost $30-40 each. NEVER buy non-factory magazines unless the gun is well known and the magazine manufacturer is well known -- do your research. Never, ever buy anything from PRO Mag.