Even if "we" were conscious for all of those incarnations it'd still feel like the first time anyway, unless you mean it will actually be the clone's first time. I hope it works like you say because I would never ever ever ever EVER want to go through all this bullshit again. EVER. For some reason I hadn't heard about eternal return until just a year ago but since I've heard it I've been seeing it a lot in other places as well. It's like when you learn a new word that you've never heard of but it keeps popping up frequently afterward. I'm very frustrated about only having heard of this so late in my life. It would've been life-saving!
I was thinking about Roger Penrose's Conformal Cyclic Cosmology (CCC). I think it really all boils down to what consciousness really is and if continuity is what defines individuals. If only we had this information now but I don't think I'd die with any peace without knowing whether it'll all be over or if my hell would be my eternity.