I generally wear Under Armour Compression Shorts, solves the problem of chafing. My cheap Performance Brand bike shorts (the baggy type, not the skin fit type) arent really the most comfortable without something on underneath.
the way the kickstand stays up is just due to friction. Icreasing the force that keeps those pieces together will also increase the friction, keeping your kickstand up. You will need to bend the bottom lip of the cup (away from the bike) that the kickstand rod pivots in. This will make it so...