Shake,
I have many of the same concerns for many of the same reasons as you have. I have been carrying daily for years now. I have several modes of carry that work for me. Although I still ocassionally carry a larger firearm in a shoulder holster under a coat, shirt, or vest, the following options are what I have used everyday in a work environment where ABSOLUTE CONCEALMENT is a ABOSOLUTE MUST. I would never carry off body unless I had a FOOLPROOF lock system in place (which usually means hard to get when you need it)
1. I have never used Smartcarry, although I think it is a great deal. I have carried a Kahr K9 and a Keltec P11 in a regular elastic waistband holster. I wore these guns in a cross draw configuration about where the pleats on the dockers are on my off hand side. I kept the waistband holster so that the grip of the gun lay directly under my dress belt . I tucked my dress shirt OVER the gun. In this position, all I had to do to draw the gun was unbutton one button on my dress shirt just above the belt line, then reach through the shirt to grab the butt of the gun from my waistband. You can use the same carry with a polo shirt, but you have to pull the shirt out of your pants to draw the gun. I ALWAYS wore button up dress shirts when I carried this way. Even when being hugged, NOONE (not even my wife) ever noticed I was carrying. I live in a hot and humid climate and this type carry always meant cleaning sweat of the gun almost daily in the summer time. So I stopped carrying that way.
2. I have decided that since the 32 ACP has 67% one shot stops (compared to 68% for 38 snubnose and 70% for 380). (Please lets not get into the Marhall/Fackler debate. I am fully aware of all the limitations of such surveys and averages.) I have since decided to carry a NAA 32 ACP everyday. I can fire 3 shots on target as fast as I can 1 from a +P 9mm in a compact lightweight gun. I am convinced enough that 3 32 ACP silvertips will be as effective on target as 1 +P 9mm that I carry only a 32ACP 95% of the time. This choice also alows me to much better carry options since the little 32's like the NAA, Seecamp, Keltec, and Autauga can be easily carried in a number of ways. (I can also carry four 10 round mags in a wallet in my back pocket. Try that with a 9mm or 380.)
I made a simple pouch (or wallet) for front pocket carry made from vinyl material. It is about the size of a check book. It is intentionally 2" longer than the gun so that while standing it "prints" like a checkbook or wallet in my front pocket. When I am sitting, the extra length of the little pouch folds over the top of the gun covering the butt and keeping it in place. The extra length also keeps perspiration off the gun 100% even in the long, hot, sticky summers that we have around here. The little wallet works perfect for back pocket carry as well. I putt a little leather "block" inside the wallet to fill out the "L" shape made by the gun. This way it never "prints" like a gun even when sitting and the little filler block also keeps the gun veritcal in the pocket so that it is always in position to be drawn straight out the top of the pocket.
Lately, I have switched to the hide in plain sight option and have been using it daily for about the last 6 months. I bought a little belt pouch like they sell at OfficeMax for digital cameras (the smallest size.) The pouch has a fully zippered compartment for the camera (or PDA) and an exterior pocket with a velcro flap that is just the perfect size for my cell phone. I carry my cell phone in the outside pockect and noone ever gives a second thought to what is in the pouch. It is convenient for standing, sitting, riding in the car, everywhere. I have never caught one person staring at the pouch in a suspicious way and NOONE has ever inquired about it. Everyone just assumes it is my cell phone. I have seen similar pouches made specifically for gun carry, but they usually don't have the exterior pocket for the cell phone. The cell phone pocket is a must for me because that is what TOTALLY "sells" this as a normal inconspicuous item.
I hope this is helpful. All these options have advantages and disadvantages, but one or the other gets me through every situation I have ever encountered and allows me to carry everyday no matter how I am dressed, where I am going, or what the weather is.
Roll Tide