I've only ever dived where I can drive or rented at my destination. I'm no longer willing to use rental gear, so will be travelling to Cozumel in about 3 weeks with my own. I'm quite leery of checking through anything I can't live without so I'd prefer to carry on the most important gear. That means a Zeagle Stiletto BC, regulator without gauges (I have an Aeris Atmos Elite, so "worst case" I could wear that on my wrist and look like a dork), and M/F/S (at a mnimum the mask, since it was hard for me to find a good fit). I don't have a problem checking through exposure gear, lights, or other easily-rented or replaced items (so I suppose that includes the snorkel). I'll definitely have check-through luggage either way, so there's no goal of avoiding that entirely.
Is it practical for me to try to carry this on? I don't currently have a bag that will accommodate my stuff that I think will be allowed as carry-on, but I'm willing to buy one. I have travelled with a full set of snorkel gear in an Akona snorkel bag since my destination was unlikely to have fins, but packed the fins in check-through on the way back. Based on this experience, the fins (Tusa X-pert Zoom XL)seem likely to be the biggest issue with getting all my gear in the overhead bin.
A rolling bag would be great, since I've got to carry another bag with medical equipment (which doesn't count against my carry-on allowance but does make it more of a pack mule experience when I tote other things), but not mandatory. As far as I can tell, the cool-looking Stahlsac, Armor, and Akona rolling bags either are too big for carry-on or don't seem intended for scuba gear as much as socks and underwear. I could be wrong.
What do people use as a rolling carry-on for a full (or nearly full) tropical gear kit?