When a bag is fed thru "the system" and gets routed to an earlier flight to your destination, it's a direct connect.
When the bag has a few hours before its connecting flight, it gets directed instead to a staging/holding area. When the time comes, it's fed back into the system for the computer to route to the bag pier for your gate.
So I ask you, which is more prone to the bag getting forgotten/mis-directed/lost ? To me, while backwards, I can see where a bag is more likely to make a tight connection than a 3 hour connection.

I tend to book long connections. I know I'm odd, but I prefer the comfort of a 3 hour layover vs a 50 minute connection that I might miss (and flying the later flight anyhow, but in a middle seat at the rear of the plane).
It's standard practice for me when I arrive at bag claim to walk over to where I see unclaimed bags being stored. Why wait 20-30 minutes for the bags off your flight to start arriving then another 10 minutes for "last bag" before considering the possibility that your bag is already there ?