Yeah I've wasted a good 20 bobby pins on safes that only hold stuff like a finance report
That's one issue I've had with this game. Bethesda seem to still be throttling when items appear in relation to the story line (I think). I broke into Rivet City's armory, used a Stealth Boy and took out the robot protecting it just so I could unlock four Very Hard containers that contained absolutely nothing. What the fuck is that about?
Either way, the experience you get from picking Very Hard locks is worth it, I guess.
Also, as far as lockpicking goes, a good technique is tapping the torque (screwdriver) to the left and hear/see the bobby pin jump but don't put so much tension that it makes it shudder. Keep doing this and moving the pick until the lock starts to give. Keep using this technique to push the lock further up but not enough to stress the pick (pushing and letting the lock drop but not all the way, keep pushing and turning). You'll eventually find the sweet spot.
On Very Hard, the sweet spot is insanely small but its there. You just have to make very small tweaks when your near the "sweet spot".