I think it's a sign that a fella has a nice little pile of money when he's traveling in a foreign country and buys a motel.
Wait, he stays there? Okay, fine. I'm sure he had visas and everything.
At this point we must understand the powerful charisma Jim exuded: hundreds of friends in a town where he was a newcomer. Perhaps everyone was fascinated by a lanky fellow with an eyepatch and a glamorous history: well, I grew up poor, then I got into cattle - not literally, mind you - then I got kicked in the head by a horse, and then we discovered oil, and I came here.
Classic grifter profile, if you ask me. But let us continue on.