words of wisdom
Don't forget to alter your arrival and departure times and parking location if at all possible since most bad guys will case you for a few days to find your weak spots. If you always park under the same light and tonight when you start out the back door and notice the light is "burned out" - might want to be extra careful. Also if you can have a second person randomly provide cover - for example they watch you open from another car (cover you so to speak) - this puts an additional level of security in your plan should they be casing your store. We used to provide this service for clients when they had increased threats in their zip code, "armed robbery rings working the area or your type of store". Also pay attention to robbery reports in your area as the bad guys find a style (MO) and tend to stick with what works for them. Especially if you see them hitting shops at closing time or on the way to the bank (cash drops).
Great insight and good points to ponder. IMO, you made 3 important points. I think arranging 'extra cover' might not be the easiest thing to do but I'd put emphasis on the street/parking lot light!! If walking out and you notice the light's out, don't assume it burned out. Assume it's been arranged that way and raise your alert level. Great food for thought there. Maintain constant situational awareness! The 2nd great point I think you brought up is changing your routine so it's not so...routine. Once you fall into the same ol' routine, it's natural and easy to let your guard down. Switch it up. And the last great point, is keeping tabs on robberies/crimes in the area, especially when there seems to be an MO.
The only other thing I think I should touch base on is the whole "gun in pocket, hand on gun" situation. You said you're pretty new to carrying and to firearms in general. Without having much experience with handguns, coupled with this method of carry can be potentially hazardous. Before you carry on the street, it's imperative that you
PRACTICE PRACTICE PRACTICE! While lounging around your house, carry it as you would on the street, U N L O A D E D! Practice walking around with your gun in the pocket and your hand on the unloaded gun. Practice drawing it. As long as it's in your pocket,
DO NOT put your finger on the trigger! Your finger better not even TOUCH the trigger until the gun has cleared your clothing! If you don't follow this rule strictly, you're inviting disaster. I seriously recommend never carrying on the street in a manner that you haven't practiced and perfected.
Personally I don't think I'd be comfortable carrying in-hand, especially in pocket. Well, depends on the gun, too, I guess. I've carried my .38 BUG in-hand, in pocket, but only for moments at a time when something had put me on condition orange. It's a DA revolver with an almost 8-pound trigger pull. I can be comfortable with that. However, I wouldn't carry my XD like that, with it having a shorter trigger pull, set at only 5.5 lbs.
When CCing, I most commonly carry in an open-style IWB in the appendix position. Most people prefer having some type of retention, and this position is the only position I'll carry in without retention. It being in the front/appendix position, I think, makes a gun grab pretty difficult. So, carrying open-style, IWB, with an untucked shirt draped over it, and with some practice; I can go from 100% concealment to having holes in center-mass in .5 to .75 seconds. Anyone can, you included. I'm just passing this on for you to think about since I feel that the method of carry described above isn't the safest. Also, if I were you, I'd consider getting a BUG. But that's me.