On the topic of Red and Ash resembling one another, Honestly i believe they are two sides of the same coin, they are the same but different. Red ages, doesn't say anything stupid, actually wins stuff, and is the ultimate pokemon master. While on the other hand you have ash. Doesn't age, is annoying and always makes a fool of himself, somehow manages to lose everything (besides the orange islands) and dreams of being a pokemon master.
The big mistake they made with Ash was that he doesn't age, i've seen it mentioned before how it appeals to the younger generation now but thats irrelevant. this links back to my point about Ash and Red being the same, Ash is the repetitive character, going through his journey, then ultimately restarting and repeating the process. While Red is the real-time equivalent of Ash, pretty much meaning if Ash aged he would be where Red is.