The plan is easy and well organized, executing it is a different matter though 
:
-Get 200-300 BTC "somehow"
-Wait for the price to reach $1,000 or so, Which shouldn't be as far-sighted like $5,000 and such
-Withdraw and exchange for USD, wait for another chance to re-enter with BTC.
well yeah, being organized would help a lot for sure, you just need to get as much bitcoins as possible :-Get 200-300 BTC "somehow"
-Wait for the price to reach $1,000 or so, Which shouldn't be as far-sighted like $5,000 and such
-Withdraw and exchange for USD, wait for another chance to re-enter with BTC.