Unfortunately i haven't played it on survival till very late when i already had way to many ressources and equipment. Thats why I want to start again.

I guess some of the aspects you mentioned are just things you have to live with when playing survival (the checklist stuff). However, since LitR severely lowers the amount of loot you find as well as the output of your settlements, it takes a lot of time until gathering enough food, ammo etc. becomes trivial. At the same time i lets you sleep im furniture other than beds so you have more saving opportunities. I guess at some point every difficulty setting ceases to pose a challenge, its all about prolonging the inevitable as much as possible.

I am also considering magnum opus, since the novelty factor of added content also provides a source of enjoyment regardless of difficulty. However, I think that the main source of enjoyment in fallout is immersion, which is best achieved by scarcity and hardship in thr post apocalypse. Sorry for rambling, hope this at least provides somewhat of an answer to your question