tikller
Sorry but no, I don't believe any current writer is good enough to create a better than mediocre story with this kind of multiple inserts in any fandom.
I don't actually plan to have multiple POVs. I just want to be them to be something the MC can face on equal footing.
Transhumanist:Oh no multiple POV is certainly doable, hell the original material is done that way. But it is very hard to do well. The author has to be very meticulous in creating the timeline and flow of events from the start just to be consistent throughout the story. So the main equation becomes this, the technical writing ability and attention to details of the author is directly proportional to how well they can handle multiple POV characters. The problem with multiple inserts is this. Think for a moment why are you writing a ASOIAF fanfiction? Because it was one of the masterpieces of last hundred years and probably one of the most well fleshed out and detailed settings ever. Every POV character the author created has been well written and came alive. So putting your own character in this setting is totally understandable, millions of fans of the series put themselves in the setting in their dreams too however much a grimderp place Planetos seems to be. So a SI in Planetos is something we love reading about. But the thing is Planetos setting is what makes ASOIAF the legend it is. You can't make it better by adding elves or Pokémon etc to the setting. The best thing that any fanfiction writer can do in the setting is doing as little as possible to change the place prior to the start of fanfictions timeline and make ever change a direct result of your MC's actions. We can tolerate the hero of our story making the setting his own, hell we like it as we do it too if only in our dreams. However we certainly hate it when an OC character rapes the setting we love and creates something that vaguely resembles Planetos for our MC to play around. So putting a modern man in Clark Kent's body and making him sour antagonist and king of Essos is certainly doable if you want to give your MC some challenge. But at that point it isn't an ASOIAF fanfic, so not something I am interested in. In my opinion this is the same for every well written setting. The moment you warp the setting and make it lose what makes it loved, you lose any potential reader that wants to read a fanfiction. At that point your potential readers are those who wants to read an original story written by tikller that vaguely resembles whatever you started writing.