My careful evaluation is typically futile and I usually end up taking the hitso if necessary I tend to take the hit after careful evaluation of course.

Seriously, it all depends as you say. If something is exclusive in another country (i.e., the Reggie's Jupiter razor that I just ordered), I have to pay whatever it costs if I really want it.
But sometimes certain items are cheaper coming this way:
The Merkur Progress and Futur I ordered, cheaper from Portugal!
The Executive shaving outlaw, way cheaper from the UK than buying it here under the Alpha brand name!
The Hone 15a, Only available through Hone in the Netherlands. On this side you can get the 15s from the Razor company but it's crazy expensive. Even that one would be cheaper ordered direct!
And another classic example is buying blades & other items from Connaught in the UK.
The Personna Gem's are made here and get shipped to the UK. Then we buy them and they get shipped back here to the USA and they're cheaper than when purchased locally. It's absolutely nuts!