Ok, so the real issue here is people might not wanna waste space because a seedling may turn out to be a male. It really doesn't seem like water logging would be an issue if your soil has good drainage. I think I'd rather risk that then having to make a mess/stress the plant by repotting. Also, about the soil you'd be using more soil if you kept increasing the size right? Small pot + 2 gallon + 4 gallon > single 5 gallon pot from the very beginning. I guess you are reusing some of the soil from the pot you are transferring the plant from, but I still think it'd be close if not more soil.