With a sidecar, traffic and terrain can mean high power at low speeds. We also carry tools, so get to meet the ones that don't make it
IMHO the technology doesn't matter, it's the quality of the bike and how well maintained. After a Rotax related walk I avoided watercooled for ten years, but the K100 suits my purposes now. So what overheats:
Bonneville- oil cooled - never
MZ - Aircooled - Never
K100 - water cooled - never
F650 - water cooled - after the load bearing lip seal went and after the fan switch stuck.
Enfield Bullet - Air Cooled - Timing was out.
Ural - Air Cooled - running on one cylinder due to electrical fault.
Ducati- Oil cooled - race clutch in the queue out of a GP meet.
R1150GS - oil cooled - had no oil in it (owner was confused by the concept, Touratech didn't sell him any, was too busy having a temper tantrum to be helped

).
The F650 is bad design. The Enfield is a combination of old design and inexperienced owner. The Ural is poor quality. The Ducati is the wrong technology. The R1150GS was a stupid owner. If Ural had tried to make a waterpump in 2000 it would probably have been a poor copy of the Rotax POS. Solution: avoid Rotax and Ural. The others were just the wrong bikes with the wrong owners in the wrong place.
I don't think you can say watercooled good/air cooled bad or the other way round, they all work when working and require next to modification in how you ride if designed for road use.
Andy