RNG can be unforgiving sometimes which would account for some of the failures, but there's also the matter of renovating the rooms for the items (spoon - kitchen, sweatbands - gym, Stethoscope - healthcare and Rescue buoy - pool) you'll find there as well. The other items from the attic have the same requirement and RNG rears its head there as well. While the items at the general store can be purchased there provided you have the money on-hand.
Possibly, but in my first play, I cheated like crazy, so it's possible I had those rooms renovated, but I recall that I fished out the swimming item and didn't have the pool, so I don't think that's the issue. And I know RNG can be a bitch but, I ruled that out after MULTIPLE days, reloading 5-15 times each time. That would mean the RNG went from getting something after 3 reloads every time (took only like 20-30 reloads in total to get every item and Libby's scene), to getting NOTHING after ~70 reloads. 5/30 to 0/75, seems unlikely.
Also, I did go back and test my current playthrough where I was at day 42, level 4, with every room you can renovate at level 4 (though not fully decked out). I couldn't get anything. So, I tested the above theory on this one too. I went in the morning, didn't try to reload and do it over, just accepted the sleeping while fishing. Literally, went same day, afternoon, and fished out the sweatbands. So, for me that confirms the hypothesis.
Somehow, it's coded in that you have to fail your first fishing (i.e. fall asleep and get nothing), and that unlocks the ability to get the night scene, Libby, and the four items you get before you finish "cracking the case." They're subject to RNG, but the RNG isn't that rough. But it seems that it's somehow hardwired into the game that you have to endure that first failure, or you will continue to have nothing but failure. Again, not sure if that was intentional, or if it's just a natural consequence of how that mechanic had to be programmed (I'm not a programmer), but you might want to add that in to the FAQ's or any official walkthroughs. I hadn't seen it ever mentioned anywhere else, but I'm not sure how many people ever kept reloading or reloaded and did other things in order to not waste a time slot getting nothing useful done.