When asking: “What does the future hold for Rory Pond?” the person to ask is not Rory himself, but Amy.
That’s not disrespectful; there now exists an easy chemistry between the two, a push/pull relationship where there never feels anything sentimental or forced about each of them (sentimentalism is different from romanticism and Moffat certainly is a romantic, if a grumpy one.)
Amy may have teased him but she never made him feel inferior for him not being as savvy with space and time travel (but as we know in The Vampires of Venice, he had read the latest papers on both) if anything his natural inclinations are magnified by his time spent in the TARDIS.
Rory is an old-fashioned hero in the way the Doctor can’t be. His devotion to Amy is unparalleled; as seen in The Girl Who Waited she is at her most beautiful when revealing that soft core underneath her brash, impulsive nature, something that manifests thanks to Rory’s presence.
In The Eleventh Hour Rory isn’t introduced as the ‘boyfriend’. He’s first seen as an incidental character already a part of the plot and in those first scenes, you warm to him as a person first rather than recognising an archetypal model for a boyfriend that Mickey often felt like in Rose.
The stakes were higher for . By the time the Doctor returned they were not casual going steady, they were nearly husband and wife and though there are similarities along both his and Mickey’s eventual paths, Rory never quite fitted the Earth-bound beau model.
It always felt, in episodes like The Vampires of Venice and, especially in Amy’s Choice , that Rory’s love of the mundane, the ordinary, the happy family didn’t marry up with his character, as if he were being position there ready for his eventual life onboard the TARDIS through narrative necessity.
Leadworth was always more a state of mind rather than a place and its homely image never really fit with the Mini driving Nurse from The Eleventh Hour.
There’s a compulsion within Rory that’s stronger than a specific place, and as we saw in The Pandorica Opens/The Big Bang it’s even stronger than an Auton’s programming. Rory embodies that super human combination and this can be seen in every action he takes in Series 6.
It’s in that season where, fortified by the memories of previous TARDIS trips (if not, thanks to The Big Bang, the experience) that Rory’s humanity and the Doctor’s otherworldliness came to a head.
In The Rebel Flesh/The Almost People Rory, despite what must be a refined self-preservation instinct thanks to his frequent brushes with death, empathises with Jenny (Sarah Smart) breaking away from the Doctor in order to protect the new life form that echoed his own memories of being an Auton.
However its in the guttural cry of “You’re turning me into you!” in The Girl who Waited that signifies the line that Rory, with all of his experience, with all the difficulties and new ways of thinking that time travel has brought about, will never cross.
He’ll never lose that humanity.
It’ll be difficult not to see Amy standing by her Doctor in the future (perhaps at the Fall of the Eleventh?) and, of course, Rory alongside her, ready to protect her and the things she loves.
Maybe the question isn’t: why does he keep dying? Maybe it’s: why does the universe keep bring him back?