Great job with all of this!
#5 is really great, and a skype could work out really well! that or a discord. Doesn't matter to me which at all but the chat that we use/used to use 50% of the time won't work for me (it won't load/crashes) so I love the idea of using skype.
#6 if counter teaming is removed, which I'm assuming the rules for challengers can only have up to 4 'counters' then just limiting them to beating a gym with that one team won't work in my opinion. People will bring in 3 steel/3 poison, 6 steel types, etc etc against the fairy gym for example and the gym leader would be stuck with 4 of one type and 2 not. If we remove counter-teaming, then I feel that gym leaders should have more flexbibility. like only required 2-3 of their type.
Or did you mean remove counter teaming, as in challengers can't really counter-team at all. Like they'll only be allowed to bring X amount of 'counters', like less than they're allowed now??
#7 I'm on the fence about. Once sun&moon come out the leagues will see an influx of challengers, and I'm worried about gym leaders being overthrown/changing too often. Whereas once it slows down again (though I feel sun & moon will keep competitive alive for much longer, maybe even longer than xy did) and then people could overthrow a leader and then become inactive. The 2nd bit is silly ik, especially since leader activity is monitored and all, but I thought I'd still mention it.
Update for the poison gym: My mother fell and severely sprained her right arm & leg so I've been unable to even look at my 3ds the past few days. Today I'm finally getting a chance so I'll be getting as much done as possible. I'm sorry for the delay