I had an issue where my wife sent an LV or Chanel purse via 2 day priority mail and it showed the same status (in transit or whatever) for a long time (like 18 days or something - I forget exactly). I paid for extra insurance when I shipped and it had been long enough (I forget the waiting period for filing a claim - maybe 14 days?), so when I filed a claim for either $1200 or $2000 (can't remember), the tracking updated in like a half hour and the pack arrived the next day.
Don't rely on what just one person at the post office says. It's like at Subway where sometimes your sandwich is great and sometimes it sucks. Half the people there don't know WTF they are talking about, don't know how to do their job, don't want to do the little bit of extra digging to figure out where your pack is, etc.
Also, not to point out the obvious, but if you're shipping through Anchorage to the continental US, that's a little more complicated than shipping from Alabama, for example. I wouldn't be surprised if the tracker starts updating at some point. Anyway, hope your money turns up. It sucks to have that kind of money in limbo and no answers.