Can anyone spare me a tip/suggestion on where to go?

So, I'm not exactly "stuck" but I'm just not sure where to go. As far as my markers go and how I organize them:

  • red marker = boss that's still alive
  • yellow marker = blocked passageway (one way or another). Unfortunately I run out of these markers crazy fast, so you'll still see "unexplored" pathways on the map with seemingly no markers (especially in fungal wastes)
  • **blue marker = point of interest. Can vary from an area that needs platforming, to an area that I think isn't fully explored, to a notable blocked area (some overlap with yellow marker), etc

Some notables:

  • waterways and deepnest I haven't explored much of, because for Deepnest all the npc kept saying its a hard area, so I decided to come back to it later. Waterways I only unlocked somewhat recently.
  • fog canyon, I'm not really sure where to go in there. Haven't found the map, but from what I can tell of its layout it's basically two large vertical spaces and neither lead anywhere. The one area I did find was blocked by the black fog door.
  • forgotten crossroads and howling cliffs, I believe are fully explored.
  • the top-most city of tears boss is the dream-version of the boss.

bosses - I know there's quite a few red dots all things considers.

I think my biggest gripe/weakness really is that it's hard to gauge how well I'm doing vs a boss, so I'm not sure if I'm sometimes "close" or faaaar from killing a boss. Because of that, I feel like I can recognize that I'm playing waaay too defensively. Like, anytime I see an opening to either hit a boss or heal; or using a spell vs saving the souls for emergency healing, or anything similar: I always choose the "safer" option.

On that note, how do you guys manage? I feel like it kinda kills my motivation for trying again. Like, with games like Dark Souls, Elden Ring, or Sekiro, if I'm getting 'close' I'll happily retry dozens of times. I LOVE the challenge. But with Hollow Knight, I tend to try 3-4 times against a boss, trying out various charmsets, and if I still fail I just move on. For all I know, the boss might've had 1% hp left.