if i saw your other post correctly, you're going to the US right? I think your "obviously...we do not trust airlines with checked baggage" statement is a bit over the top, no offense. Given the valuable nature of the stuff you're taking to the US, I think you should just check the stuff and don't worry about it. I check valuable things in my luggage all the time.

I don't know what regular HK security will do, but the secondary screening for US flights can be random. It's usually harmless. I go through it every 4-6 weeks in HK and I will say that most times, they just do a cursory check of your stuff and let you through. However, there are the handful of times you get a screener who is incredibly anal or just having a bad day, and doesn't let your stuff on. I was once forced to open a a box full of tea (I had the receipt, I had just purchased it in HKIA, screener didn't care), which was a bummer since it was a present. Another time I got my deodorant confiscated...despite having taken that identical brand of deodorant with me to the US in each of my other 25 or so trips in the past few years. So my point is, you're kinda up to the will of the person checking your stuff. Normally it's fine and they don't care about stupid stuff like that....but if you have bad luck and get someone who says "you're not going on the plane with that pin" (I presume it's sharp and pointy?), you're not going to be able to do anything about it and worse yet, the plane will be ready to depart so you won't have much time to figure out a contingency plan.

My calculus is odds of losing it in checked luggage < odds of losing it at HKIA during regular or US-specific security screening.