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Good questions. Some theories...
1) The first ability that comes to mind is the 10th level barbarian rage power Body Bludgeon, which lets you hit someone with someone else. I do recall I once saw a build that stacked that with an ability that let you hurl your melee weapon (I can't remember which ability) to hurl crocodiles around the battlefield (Build was also part druid). That would set this ability at around a level 10 feature, so if I were homebrewing I would start with a new feat for a 10th level character. There may be another way to do it. Awesome blow, maybe? Could always modify the prereqs to something achievable. Lemme think about this. Are you looking for a homebrew solution or a rule-as-written option?
2) I can't find a reference to Stiletto Boots anywhere, but I see no reason why not. It's not giving you anything that cannot be acquired on a normal weapon.
3) I think so. You're essentially taking a roundabout route to acquire a weapon with the stats of a punching dagger. Doesn't seem out of line at all. I support it.