Just start wherever. It's the same formula, and they all do a pretty good job of easing you in.

I completely agree here.

Also, if you want to make the game a bit more interesting, once you complete yellow and understand how the game works a bit, use a modified rules for the following entries.

Basically, there's a user imposed rules (I forget the name) but the rules are:

You can only catch the first Pokémon you encounter on each screen. You cannot revive fainted pokemon. And you must name all the pokemon you catch.

It's a bit hard, so I might suggest you change this to:

Can catch any five you first meet in any area. Must let all but two go once they are all caught.

Cannot revive at the pokemon center.

Must name all your pokemon

It makes the game way more interesting.

Ah, good ol' Nuzlocke Challenge. I've done it a few times. It was fun and very heart breaking. I hope to start a comic based on one in time....

It really is the best way to play it.
Nothing sadder than losing your favorite.
Also you better hurry up because somebody already made a comic of it.
Although I'm sure there's always room for more ;)
Gl

Yeah, I've heard there were quite a number of comics and stories made already, though no 2 stories go the same. So there's room for all sorts of funny and sad comics and stories xD

Actually after thinking about it, starting with Red Blue can actually be bad as you'd be getting used to it's terrible balancing that's fixed in later games. The farthest back I would go is Gen 4 as that's when Pokemon finally started making sense, but even then, the biggest draw to Pokemon is the multiplayer, so getting the latest version would be best.

There's also a bunch of bugs in Gen 1, which can be frustrating. Make sure you look up those kinds of things before you decide.

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.

Fire Red definitely!!!! Oh how I miss you Kanto T_T

X/Y