You can't compare riding barrels surfing (advanced) to simply moving back and forward behind a kite (basic). Both sports have their hard parts, I would say neither is really harder than the other to be really good at, but kiteboarding certainly has a lot more variables to contend with when learning the hardest tricks, which in my opinion can make it more difficult depending on location.
As Elliot says above almost any gear can do kiteloops. In the beginning we all tried to do Kiteloops on 2004 C kites that would hardly ever catch you as you fell out of the sky

. Just try it in not overpowered conditions and see how it feels, step it up slowly.
p.s.
The hardest boardsport to be pro level at is by far Skateboarding.