iPad Question from a newbie point of view

I started a thread a few month back in which I was finally told the only way I could update my iPad2 on 4.3.5 would be through iTunes. Waiting for the next jailbreak to be released, i was wondering what could be the best move. Update first through iTunes (btw could anyone tell me what is the current ios version one can update his iPad today?) then waiting for the jb to be released which could last months or never OR wait first for the jailbreak and then update but considering the last option, by the time the jailbreak is available, wouldn't Apple release a new ios soon afterwar? Any help to sort this one out?
Thanks

braddick said:

You have a rare machine as it stands and one you may want to pitch on 8.3

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As a non english speaker, I m not sure what you mean by pitch on. Do you mean stick to the 4.3.5 i am currently using and forget about any update or update to the last ios version 8.3 with no guaranty it will ever get jailbroken?

eyoungren said:

He is making the strong suggestion that you stay on your current firmware.

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Ok, I get it now. Sticking on my current firmware may be the best option but who is getting frustated about it is my son as no games is released for it anymore.
Thank you for your lights
btw, could you anyway inform me about my dilemna exposed in the first post?