I would like to see two different versions of Baloo, one from The Jungle Book and one from TaleSpin, and then have a friendship between the two.
No. That’d break the timeline.
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What timeline?
The one in DHBM. You can’t have Adult S&N meet Young S&N, right? It’d be strange. Same thing goes to Baloo from the past meeting Baloo from the future. Or whatever relationship The Jungle Book has with TaleSpin
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With Jungle Book and TaleSpin are and are not the same characters. Names and personalities are the same (mostly) but the TaleSpin characters are only adaptations of their namesakes and are not the actually the same characters.
But it still wouldn’t make sense for two versions of the same character to be friends with each other.
Clone wars in DH:BM!
Remy vs Remy and Gerald vs Gerald 
And no, as @Filadae_Djaq said, it will break the timeline, two exactly same characters can’t be added.
But TaleSpin version of Baloo would be better, and only this version, but for Jungle Book fans, movie version can be his costume 
For same reason Kiara and anything from The Lion Guard won’t be added.
Iago isn’t in bad side.
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Again, it’s just my opinion, but I don’t consider them the same any more than I consider Cruella de Vil or Madam Medusa the same. As many may know Disney has a history of copying and reusing the same character, just under different names and sometimes genders. The only difference between them and the Jungle Book/TaleSpin characters are that with Jungle Book/TaleSpin they kept the names.
Again, it’s just my opinion. But the real decision will be up to the devs when it comes time.
Yeah, sure. List every one of them.
I would like to, but I don’t know all of them.
I do know that Madam Medusa was copied from Cruella de VIl, I also know that Jafar and Frollo were basically Maleficent and the Wicked Step Mother as men. I know that Tip and Dash are just Timon and Pumbaa as a penguin and walrus. Also, since Jasper and Horace almost anytime a villain has two henchpersons, they will basically be Jasper and Horace in a different form.
In the case of the henchmen, they have varying levels of competence.