1.) I have, say, Gin Genie with Escrima Sticks (which are Transferable) in play on turn 4. I play U-Go-Girl, Tragic Teleporter. and bounce Gin Genie back to my hand to bounce my opponent's 2-drop back to theirs because that's what UGG does. Can I put transferring the Escrima Sticks from Gin Genie to U-Go-Girl onto the chain when I play U-Go-Girl? (By my thinking you can, much for the same reason you can chain double effects when Dr. Doom, Diabolic Genius hits the table.)

2.) On turn 5, I have U-Go-Girl and drop Anarchist, Tike Alicar while I have X-Statix Cafe and Star of the Show in play. I have initiative so I team attack their 5-drop with Anarchist and UGG. I play Grandstanding, KO UGG, and Anarchist is now hella big - 19/17. Is this still a team attack (meaning Anarchist does no breakthrough, but KOs the defender if the defender is stunned) or not (meaning breakthrough but Anarchist's power isn't triggered)?

No, the transfer mechanic is a triggered power that triggers at the beginning of the Formation Step. You have no control when it triggers and can not just transfer it at your option.

Yes this is still a team attack so no break through, but Anarchis' power will still trigger and KO the defender.

Just a note though, Grandstanding doesn't KO anyone, just stuns, so you wouldn't get the bonuses from Cafe and Star.

But anybody stunned during a team attack with Anarchist is KOed. ha HA! :)

nope, ONLY if they are stunned by an attacker or defender. So you stun your guy for Grandstanding, he doesn't get KOed since he wasn't stunned by either. It's really a very good card with Anarchist.

you could use Mind over matter after grandstanding, return her to your hand and make Anarchist a 22/17 with flight and range.

true, but since you're team-attacking anyway there isn't much need, since you won't do breakthrough.