Dealing with the guilt Kirk feels over women he loved and lost is very much a contemporary type story where they feel the compulsion to explain or rationalize the hero's behaviour. They are effectively trying to make him seem less of a bastard.
This is the challenge of trying to write for a show created fifty years ago because inevitably contemporary perspectives will creep into the production. It's a contemporary perspective trying to "fix" perceived past mistakes.
I never thought Kirk was a bastard because of his past relationships and that some of them died. As such I didn't see the need to have it explained what whatever guilt he might carry might do to him. But that's me and I can see how someone else might believe otherwise. And so then it comes down to execution.
In TOS we never got to see a woman commanding in Starfleet except for Number One. After that it was never explicitly stated anywhere that a woman could not command, but for whatever reason the writers never chose to again explore that possibility. Since then writers have addressed this issue by creating female characters in Starfleet command positions during the TOS era. And now the fan film productions are also doing it. They are responding to a possibility not more fully explored in TOS after "The Cage." In this case they're not really injecting a contemporary idea because the idea was already there all the way back to the beginning. The holodeck is another example of exploring an old idea never realized originally.
There are any number of ideas mentioned or not fully explored throughout TOS that could be the springboard for wholly new stories. But even then there are limits and you then have to resort to contemporary ideas explored in the TOS style yet still seem like something that could have been done back in the day.
This is the challenge of trying to write for a show created fifty years ago because inevitably contemporary perspectives will creep into the production. It's a contemporary perspective trying to "fix" perceived past mistakes.
I never thought Kirk was a bastard because of his past relationships and that some of them died. As such I didn't see the need to have it explained what whatever guilt he might carry might do to him. But that's me and I can see how someone else might believe otherwise. And so then it comes down to execution.
In TOS we never got to see a woman commanding in Starfleet except for Number One. After that it was never explicitly stated anywhere that a woman could not command, but for whatever reason the writers never chose to again explore that possibility. Since then writers have addressed this issue by creating female characters in Starfleet command positions during the TOS era. And now the fan film productions are also doing it. They are responding to a possibility not more fully explored in TOS after "The Cage." In this case they're not really injecting a contemporary idea because the idea was already there all the way back to the beginning. The holodeck is another example of exploring an old idea never realized originally.
There are any number of ideas mentioned or not fully explored throughout TOS that could be the springboard for wholly new stories. But even then there are limits and you then have to resort to contemporary ideas explored in the TOS style yet still seem like something that could have been done back in the day.