Metagame issues are often not mathematical, so you can't expect to calculate much. If you are playing against someone who plays you often, then the metagame is more important than against a reg whose playing hours do not overlap yours much.
A casual player who sees you resteal with a speculative hand is more likely to make spite calls against you in the future, perhaps because he doesn't understand risk aversion, and will suspect that you have a wide range whenever he see you push in the future. However, a reg might not react the same way. A reg who sees you push with a weak hand might not want to have much of a raise/fold range. The reg will steal less, while calling more, and might start pushing deeper. Although you might not want to get called more, you will enjoy more walks, and it is not clear that the net effect of the adjustments will be bad for you.
Another consideration is that you only get caught about 4/22 of the time if your opponent is raising a 22% range and only calling with the top 4%. So, you get the benefit of pushing about 5.5 times for every time you get caught.