It's been an embarrassingly long time since my undergraduate statistics class, so the math might not be 100% correct, but I'd like to attempt it anyway, be sure to tell me if I'm wrong:
Worst case, you fly twice a month for 20 years, that's 480 flights. Each flight is a round trip, so baggage is entered into the airlines systems 960 times in 20 years.
If the probability that an airline gets your baggage to you each time is 99.99%
.9999^960 = .9085
1-.9085 = .0915
So, if my calculations are correct, in 20 years time, there's a 9.15% of chance your bags having be lost at least once. Assuming that the odds of an airline losing all bags are the same - and they are obviously not.
Anecdotally, luggage does miss connections on a fairly regular basis and if there are airline changes/international flights involved, it may take a few days to track a bag down. But I've never had a bag lost permanently and I can't remember the last time I've heard someone I know complaining about that happening. I think my parents in all their years of travel may have lost a bag permanently once.
ADDED: The statistic in the article doesn't really say what percentage of luggage is lost though. The quote is “Less than one-half percent of bags are ultimately unclaimed." So this is the case where they have the luggage but can't figure out who the owner is for whatever reason. Presumably other bags are just lost--probably most typically stolen.
I was answering the GP's question if they are just lucky or if they can expect lost luggage with 20 years of regular travel. The answer is: the odds are highly in your favor of not having an airline lose your bags, even after 20 years of regularly entrusting your bags to the airline.
One time my bag was delayed by a day and an airline representative delivered it to my home, which was nice. Another time I volunteered to be bumped in exchange for a voucher but my bag was already loaded so it arrived significantly before I did.
But even taking into account the improvements there, there's still a bunch of sleep deprived humans at the end of your 12 hour redeye who are happy to take your bag if it looks a bit like theirs (this happened to me even though I covered my bag in unique stuff...)
Rule 1 - Pack light and just bring a carry on if possible.
Rule 2 - If you are connecting try not to check any bags.
Rule 3 - If checking a bag make sure you tag it with your flight number, home address, destination address, phone number, and record locator number (this one is important).
I can't wait for the day of fully autonomous cars. Anything within 8-10 hours driving would replace flying for me. My trip was a 2.5 hour flight and took 12 hours to get there before it was all over.
The value of the luggage was much more than I would have expected - clothes add up in cost - but the work travel insurance covered everything. It was a hassle re-buying all the stuff I don't use very often, after I'd put that task off for over a month hoping the bag would turn up somewhere.
That being said, I believe, IIRC, the airlines are supposed to compensate you some amount when they lose your bag.
You're right though, clothes really add up, especially if your stuff is higher end
I wanted them to pay, since they lost the bag, but it took so much time going through their convoluted systems that eventually I had to accept I was wasting work time, and should claim on the work insurance.
The only one “lost” permanently (had many lost temporarily) was put on an earlier flight than mine. Fairly likely wasn’t lost by airline / airport, but rather stolen. Conveniently the cameras near that carousel weren’t working that day.