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1) Depends on the seller (all non-Amazon sellers have their own inventory controls).
When shipped directly from Amazon, they seem to be shipping with a firmware version that currently can not be jail broken.
If you should get one of those, you can still use the OTA update blocking name to keep it at a selected version and then just wait.
All models, with the exception of the two Oasis models, can always be jail broken using the serial port.
2) Yes - either now or sometime in the future (only the most recent Oasis model is in the "sometime in the future" category).
Like, we don't have a paid staff that works to set production schedules.
Extra:
Of course I don't know how your mind defines "nicer"; but the PW-3 is still the best selling device and still the best value / price combination.
Also, it is only a few months short of having been on the market for three years (a long time in the world of e-book readers).
Which means there is a good market of used and re-furbished devices (which **might** still be running an earlier firmware that can be jail broken).
After three years, **everything** works on a PW-3.
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