The teachings of the buddha are of great depth- it is also a gradual path.
There is also the concept of going from what is good, to what is even better in the teachings -to keep improving. ('ujuca sujuca')
So be at a stage which will almost guarantee a good rebirth (sadd, sila, suta, cage, panna). Once you are there and well established in that, you will need a further challenge! Keep improving yourself- only stream entry can gurantee a good rebirth.
Then again going for an extended retreat in Burma, perhaps with Mahasi sayadaw camp or the Pa Uk camp fir 3 months is not beyond reach if we really want it. Sometimes it helps to be in that environment which is optimally geared to motivate us to practice.