I used to have an olli and a Monterey... I liked both for different reasons as well.
rigid latch is instinctively easier... just push the seat in, listen for clicks, you're good to go.
However, not all vehicles have their latch connectors positioned to make it really truly that easy... so to not have to bend down and squint and carefully push in one side, then the other, I like the flexible latch for vehicles like that.
and... yep.. ANOTHER However... I also think that it would be nice if Clek did as Cybex does and offer the plastic guides for the latch connectors... however, not sure how MUCH easier that makes things for the issue I referred to as you still have to bend down and look where you are putting them... and I doubt anyone would leave the guides there when the seat is not in use... so really doesn't cure the issue.
For removal, I loved the rigid latch... whether it's a strap, or reaching and pushing the two buttons, it's less complicated than the flexible kind where you have to push the lever, maneuver the seat forward, then unhook each one. (this may be less so annoying on the parkway sgl, as it has the push-button latch and the straps are on the side, making it easier to do all that, but still, there's a convenience factor.
Anyway, that's my experience.
I'd love to have latchable boosters for Ruthie, but she didn't fit the Monterey, the olli I had would have probably expired before she'd have ever used it since she's far more petite on the charts than her brothers (though I may splurge and buy her one or two (depending on how doable hanging it in the house and taking it to whatever car she's going in would be) when she eventually outgrows her highback boosters), and I could not afford an Oobr or the Cybex.
The upside to a non-latch booster is that they are typically lighter weight.