i know its seems silly,but it's true bigger is better,and like you said in mostly dressage/hj...in h/j the bigger horses have the stride to make it better in the strides required for hunter and in jumper they cover more ground and are able to finish a bit faster then their smaller counterpart.and the bigger horses seem to make higher fences less intimidating
bigger horses in dressage are about the ability to the more advanced movements at higher levels and do them well and have flow and balance.a bigger horse seems to be more flashy and presence alot more exciting.IMO
i agree with you on the height rider vs the height of horse comparison..as i used to ride a 17.2 tb mare and i am only 5'feet tall.i felt very small and actually felt over horsed in height sometimes...i was in 4-h at the time and got some pretty weird looks...so really she was kind of tall for me..
i feel small on anything 16.3 and over.16.2 is my limit as far as rider:horse ratio.
there also seems to be more opening in terms of showing(classes) as well,as i've seen and heard.
i am also not saying a smaller horse can't achieve above what i said,just that a bigger horse might have an advantage.i have ridden and seen ponies and horses(under 16h)that do quite well at dressage and h/j events etc.
actually don't also know how the trend of bigger horse is better trend started.that will have to be answered by OP.hope this helps on some respect.