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I am a firm believer that your bankroll is way more important than skill when you're choosing what level to play at and when to move up/down. It's all about being comfortable with the bigger buyin. If your bankroll can't handle it, then your game will suffer. If you're killing the $16 two tables, then you should have no trouble at the 27s. I can say from experience that there's not much difference in the level of play between the two.
Good luck. Playing poker full-time is way better than working, but don't be too discouraged if you fall short. I plan on working and playing simultaneously this summer. If poker really starts to swell, I'll quit working and just play full-time, but I'm recovering from losing almost my whole bankroll in a horrific downswing since I switched to playing MTTs full-time so my selection is pretty limited right now.
Yours is an ambitious goal. Keep us posted.
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