Re the 'clubbed' & 'dropped' hooves, as with everyone, horses are very rarely(ever?) perfectly symmetrical. Also, like us, they automatically favour one side - eg right/left handed. So, with natural inclinations to stand with a particular foot forward, body issues, etc, they do often tend to have one fore more upright to the other. I wouldn't consider the 'high' foot necessarily a 'club', unless it's severe. I also wouldn't try to match the feet to eachother *at least without a good bodyworker to work with the horse too. Just because the 'low' foot is low in the heel doesn't mean it's too low(you'd need to assess the bones inside), and just because a hoof is higher than 'ideal' doesn't mean the heels should be lopped off.
What does tend to happen with 'high/low' feet is that the 'high foot' toe flares forward, which is it's inclination, as it's the 'back' foot with more pressure on the toe anyway, but often farriers do try to match them, encouraging this further. The toe should be kept in check, in balance in relation to the bones, regardless how high the heel may 'need' to remain. The 'low foot' is also inclined to 'run forward, both in heels & toe. Unfortunately, depending how it's done, wedging can not only be unnecessary, but further exacerbate crushed heels.
This horse may be 'clumsy' for a number of reasons other than his feet, but commonly, high or crushed heels are quite weak, so it could be that he needs protection under his frogs. Or it could be about balance, particularly if he has long toes to trip over. That he seemed worse with the wedge could be about the different pressure on his feet, or about the different body balance & that he was out of balance for what *he* needed. Could even be that something was hurting, due to forcing a body not used to it to be more symmetrical.
As for 'trying barefoot', you've probably already heard me say I think (conventional)shoeless is best where possible, but that's not to say it's always the wrong choice, or that barefoot is best. Horses very frequently need protection/support in some situations at least, to do all we ask of them. If your horse genuinely seems to have good, strong feet & do well bare, by all means see how far you can go with that. But if your horse has unhealthy feet, they're sensitive on stones, they're thin soled, etc, I think it's best to assume they need boots or such when ridden, and take 'trying bare' carefully & gradually. It's all very well talking of 'transitioning', but I don't think just forcing it on them is reasonable, and what if, due to damage, lack of development, environment, etc, the horse is not at the point where he CAN grow better feet yet & handle what you want without further risk of injury?