I don't know if the subject is open to much speculation. They already made that episode, only the Borg ship was round and yellow.
I suppose it all depends on how much you want to lean on the novels. How canon do you consider The ShatnerVerse?
I'm hoping this* is the plot of Star Trek XIII. *With reimagined, super terrifying Borg. No more Uncle Fester makeup and rubber suits, but using CG to replace body parts with steampunk machinery.
I'd love to witness Kirk trying to hit on the Borg Queen and turn her away from her "evil" ways then, during the throes of their passion, to have her assimilate him.
I can just imagine the blinding camera flares all the NuBorg bling would cause, you would be able to look at the screen
1. Kirk poses a logical conundrum to the Borg and they go into sleep mode. 2. Kirk tricks them into computing a very large number for the same effect. 3. Kirk seduces the Borg Queen. She gives him implants. He gives her space herpes. Kirk wins. 4. Kirk uses the Corbomite trick to stave off an attack and to buy time for Mr. Spock to figure out the rest. 5. Enterprise goes back in time. Kirk spreads his genes across the star systems that are in the path of Borg conquest. The millions of children of Kirk are too individualistic (i.e., narcissistic) to be assimilated. The Borg change direction, sparing the Alpha Quadrant.
There are so many things I could say to that, but could be a little overwhelming for those of a nervous disposition
I'd actually like to see this happen in the next JJ movie. With today's special effects and make up budgets. A creepy reboot of the Borg. Since Kirk's the only captain not to face them in canon, it's about time he got his chance.
That's up for debate. Some believe the scene in Generations where Kirk and company are rescuing Guinan and the other Elurians, was directly after the Borg's assimilation of Eluria. If that's true, Kirk would have indirectly dealt with the Borg right before he "died".
But then why did Q have to port the Enterprise D all over the galaxy to meet the Borg for the first time? They couldn't have been that far. Guinan appearing in Generations like that never made much sense to me but I'm happy to ignore that. I still like Generations because of all the TNG movies it captured the mood of the series the best.
Maybe the Borg's focus was elsewhere during Generations and Q's gift was a head start of things to come. I wish I could find that thread, they bring up some interesting points (even though I was on the side of the Borg came much later).