Its seem like u still not understanding pebble well and does not know what u actually want. If u asking for ans like per ur stated above, i would say buy all of them and fiddle with it urself. Otherwise u opt for andriod smartwatch or apple watch since they are more towards all rounder watch. 😁

Just a headup for you, pebble 2 is mono display and pebble time 2 is epaper color display. Refer to below hardware spec;

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Of coz. Unless u add on a 3rd party using smart port to have wireless charging.

Yes. You need cable to charge. If it follows the same kind of mechanism like the current generation of pebble, it is super easy as the contact is held on by magnet. It is a pretty good system. Pretty flawless. Second best to wireless charging.