Ok, maybe I should have asked if anyone has personal experience flying tanks on Southwest.
As mentioned, if the valve has to come off for travel, it needs to go back on with the appropriate torque and I won't have those tools available. Getting a dive shop to do it will probably involve getting charged for VIP/Hydro too.
The places I'm most likely going after Cozumel (Mahahual/Xcalak/Cabo Pulmo) don't rent steel tanks. I'm an air hog. I dive with some guys who have 15-25 years experience and thousands of dives. I don't think they breathe at all. Every dive I go on with them will either end short or involve me diving my air and waiting on the boat for 15 minutes.
Southwest allows two 50lb checked bags for free. An HP100 weighs around 38lbs empty and Southwest has no problem with you checking them, provided they are empty and packed well. That means I can still pack another 24 pounds in my checked baggage. And I'll have plenty of room in my two carry-on bags for everything else I'll need.
So yeah, they're heavy and a PITA, but unless someone in PDC/Cozumel is willing to sell me a couple of HP100s for $300 each, this is my main option right now.