Help appreciating the value of a jailbreakable/jailbroken PS4

I'm challenging myself to assess my valuation of acquiring a jailbreakable or already jailbroken PS4 and have come up with what may amount to be some potentially noobish questions:

1. I know nothing is guaranteed but, how reliable are the OFW versions for the various bundles according to crowd sourced data? If I were to find an older NIB bundle (e.g.: Dynasty Warriors 7 Bundle; Destiny Bundle; Watch Dogs Bundle etc.) that, shipped, with 1.76 or 4.70 or 5.05, how likely is it to...

Help appreciating the value of a jailbreakable/jailbroken PS4