Heartgold and Soulsilver would be the best place to start. They are the Gen II remakes, and you can say you kill two birds, if you aren't too interested in the Gen I story. Then the best option would be to jump to Gen IV and Gen V which are the DS games, jumping Gen III because you will play that in ORAS, but if you have a GBA and can found Emerald then go for it. Then pass to XY and ORAS which are the most recent, and of course, afterwards get Sun & Moon. Then if you are interested get the Gen I games in the VC. So pretty much a order like this:
- Heartgold/SoulSilver
- Diamond/Pearl/Platinum
- Black/White
- X/Y ORAS
- Sun/Moon
- If desired Red/Blue/Yellow.
Though just don't begin with Gen VI (XY) or Gen VII(Sun & Moon), since then you may have a hard time accoplating to the older games, since they can be slower in certain things than the newer ones, which makes sense seeing how they are older.
COMG guide to points: 1 point = Raging. 2 points = Beasting. 3 points = Tearing it up. 4 points = Berzerk. 7 points = Rampage. 12 points = Burst. 15 points = god mode. 20+ points = DIVIDING BY ZERO!!! 40+ points = Youkai (originally Pokemon).
-1 = Negabeasting. -5= NegaRampage. -10 = NegaBurst
