All the Robins have had futures where their Gotham is peaceful/crime free besides Tim. Some like Damian have more than 1 crime free future Gotham it doesn't mean that the next Bad/evil Batman isn't going to be Jason or Damian or Tim.
Any of them can be written to cross the line. The thing with Jason is that he doesn't ever qualify as heir to the Batman cowl so stories of him inheriting the cowl are... well just one.
If you're talking about Countdown, I don't know if an alternate earth would count as "future". That said, the two futures we've seen during N52/Rebirth showed Jason either warring an endless, one man war against crime (Future's End) or like a broken man that could only provide support to Batwoman (Detective Comics)
The 90s really established that problem. The thing about the Bat-family is that, while it is easy to establish each character into his or her own "corner"of the DCU, it becomes increasingly difficult when it comes to event storylines/crossovers to bring everybody back. It is why, despite giving Dick his own city, they established Blûdhaven as being a 40 - 60 minute drive from Gotham. This allowed him to do his own thing and still be able to pop up in Gotham at a moments notice. Just easier for the creative teams that way. Look at the headaches they went through in constantly bringing the then world hopping Azrael back to Go5ham for major events.
The Flash and Superman families can get to Central or Metropolis in a instant.
Simone Di Meo's Harley:
Do we even know if it's Harley and not some "new" Harley ?
Also, it's kind of sad that Batman's future State seems less interesting than the Super and Wonder FS books, because it's too concentratred around one event, instead of offering us a wider range of stuff to discover...
I really like the new look on all of them for those issues. I like the idea. Can't wait to read them!