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Only you can decide how much risk you are willing to take. Let's look at some specific examples:

1. 30.06 printed on 8 1/2"x11 piece of paper.
2. 30.06 and 30.07 wording mixed on the same sign
3. 30.06 sign not posted at an entrance but buried in a hallway with the building - letter size and wording are correct
4. 30.06 sign still has previous version language
5. 30.06 sign has proper sized letters and wording but is put on glass near entrance with nearly transparent letters that are impossible to read unless you are standing directly in front of the glass and know that the sign is there. Because of the background, the words do not appear if you are standing back from the glass 5 feet.

I've personally see all of these. I've chosen to ignore some but not all of them. I have to admit that I've gotten a lot more sloppy about concealment since OC passed. I would not have gone too many places printing significantly before and now routinely don't care how much I print as long as the gun is covered when I'm at least attempting to conceal. If I were to decide to walk past a non-compliant sign, I would be a lot more picky about my concealment. As a general rule, I don't consider walking past non-compliant signs because i really don't want those merchants to have my business, not because I'm concerned about their signs. Another factor to consider is how militant the merchant might be. I believe that some places put up signs and maybe even non-compliant signs because of corporate directives that local management might not agree with. Sprout's Farmers Market is not one of those and they have a very "iffy" 30.06/30.07 on the sliding doors. When the doors are open, the sign is almost impossible to read but I believe that they are such a progressive mentality company, any of the clerks would alert their management if they thought that they saw a concealed handgun. That said, I'm not sure that they are either observant enough or skilled enough in knowing what to look for. Whole Foods is another with a questionable sign but a militant mentality. Still good concealment would likely never be spotted.

Depending on where you are, if you are detected, the DA's office may do like NJ and NY and decide to make an example of you. The new DA in Dallas, I believe, would be one of those. My own local Chief has said that his officers would look at the sign and if it didn't comply, no action would be taken. We specifically talked about letter size, contrasting letters and wording. I would be less inclined to walk past a non-compliant sign in Grapevine, where the police leadership doesn't seem 2A friendly than Lewisville where the police leaders have spoken at local meetings as 2A advocates.