Quick Update:
I finally managed to grind almost my entire team to level 40, then attempted the elite four. I made it to Bruno and his Hitmonlee, but he demolished my entire Ice-team, with a combination of Blaze Kick and Hi Jump Kick.
I went back and raised my Jynx up to level 44, then tried again. This time I wiped Bruno no problem at all, except his Machamp was a little tough.
The Dark-type E4 member was pretty easy, the only threat on her team was Houndoom, who was doused easily by my Lapras and her surf, while holding Mystic Water.
Lance and his Aerodactyl gave me a bit of trouble, until I sent out Mamoswine, who cleaned it up. My Glaceon and his Hail, blizzard combo took out all of the rest, except Charizard. Who, surprisingly, stood up quite well, but was eventually taken down by my Lapras.
So yeah, I have made it into Kanto. Here is my team, as it stands:
Lapras, level 43. Ice Beam, Surf, Waterfall, Thunderbolt
Glaceon, level 44. Ice Beam, Blizzard, Icy Wind, Hail
Cloyster, Level 41 Aurora Beam, Clamp, Withdraw, Supersonic
Mamoswine, level 44. Earthquake, Ancient Power, Avalanche, Strength
Jynx, level 46. Psychic, Shadowball, Sing, Blizzard
Weavile, level 40. Faint Attack, Night Slash, Icy Wind, Thief