I'm having the same issue. I have a TTG account, and I used cloud sync to save my game.
I originally finished season one like 2 weeks ago, and I was unable to import my game, so I looked up the help on the TTG website and it said that if you go back and change choices in any chapter, you have to replay all of the game following that change in order for your save to be valid to import: telltale.com/support/article/mc2-save-import/
So, I played the entirety of season one from start to finish without altering any past decisions, and I still can't import my save. At this point, there isn't any way I'm going to replay season one a 3rd time, so I guess I'll be using the recreate feature, but I can't say I'm not disappointed by that. I really wanted all of my choices to follow through and it seems like the recreate feature skips over a lot of details.
It has been kinda depressing, and frustrating, and has really sapped my motivation to continue playing. :c
I had been using their website to track the progress of my save, and it was working fine up until chapter 7 at some point, then suddenly all of my choices disappeared from their website.
According to the link above, you should be able to import your save right after having finished chapters 1 through 5 of season one. Maybe if I take a month break, I might go back and try that and then just not do chapters 7 and 8.