As for whether it SHOULD happen:
On paper it seems like a good idea, since it was an Off-Broadway hit with a high-profile cast, at a time when Sondheim revivals are in-demand.
But I don't think it would do well commercially in a larger house. The cast is starry for Off-Broadway, but not enough to sell out a limited run on Broadway when most of its NY audience has probably already seen it. I know people might mention the in-demand lottery and the sold out extensions, etc. But IIRC, the cancellation line was very easy, sometimes non-existent, and tickets weren't so difficult to come by if you kept your eye on the site. That doesn't bode well for leftover demand.
And the production isn't bold or interesting enough to warrant a transfer to a larger space. Aside from the cast and the material, its strongest point IMO was the intimacy - not just to the actors, but to the folksy instruments. I don't think it can be replicated on Broadway (no, not even at the CITS, since I know people will inevitably suggest it!)
Whether it WILL happen though, is another question. MUCH stranger things have happened. This season alone had probably 8-10 other shows that were less likely to transfer than Assassins. Most of those shows have been doing badly, but that doesn't seem to stop people as much as you'd think. You really never know which projects people will put money behind.
One thing to note: it seems unlikely that they'd record an album if they were planning to transfer. Most musicals transferring to Broadway will hold off on recording an album so they can market it as the "Broadway Cast Recording," and to help the album reflect the "final product." It's not unheard of, but it seems unlikely for them to transfer after having recorded the Off-Broadway album.