Powershot, your responses reminds me of LucifierIX on ff.net He writes the same way you do, well similar. Maybe you two might get along well together. XD
How would Ash and May look if they were older? (Can be any age. 20, 30, 40, etc.) And how would their lives be?:
Depends on your perspective of 'older' Some like to see a 20 year old all buff and hot while others see a 20 year old still acting like they were 17. To me, if I do write a story where I say "Ash is 20, May is 18" which I don't do that much of anymore I would make sure their appearance would look different in each story I write. Like for one I might make Ash 20 but he still acts like he is still 10 while in another he is cold, snobby and mean. Same rules apply to May or to any character really.