If you start at the beginning, that's fine. The games are timeless. You can play them forever. I do it all the time. I frankly own every game version. But, if you decide to jump to the current games, after them. You're gonna get slammed with all the changes. If you are adamant in starting from the beginning. You really have to stick to playing them in order. All the added stuff over the years. Gets really confusing, quick. If you jump around.
The benefit from this is: Once you reach Gen 3 and Gen 1's remakes. Gen 1 and 2 are orphaned from the rest. There's save file editors which you can use to recreate your Pokemon, from Gen 1 and 2. I've done it. But it takes a long time. But anyway, you can keep all the pokemon you get. If you have all the original hardware. You can keep transfering them over and over again. Till you reach the current games. I have my Swampert starter from Gen 3 in my X/Y games right now. And still use it. Plus, all the mystery gift and store events, over the years.
