While waiting, I went ahead and reused the same Save I was talking about. It's close, but you have enough steps to get everything. Maintain your stats and fight the boss. Can't Save again after picking every little trinket up though. You'll lose a stage of weight.
That all being said. I think I've realized a simple enough solution to this 'impossible' challenge. The main reason this boss feels so difficult, is mainly because you're on equal footing, sort of. The hero does 50 dmg, the boss does 40. Boss has 400+ Hp, Hero has 500+ Hp. If it was as simple as spamming attack. Then you would be able to win every time. However, since the boss spawn's other mobs. You have to focus on doing more than just attacking. Regardless of what you do exactly. You'll wind up getting into (or close enough) risky health territory. Around the time the boss spawns even more mobs.
I think an easy enough solution to avoid this. Is 'rewarding' the player with a medium potion. From the tutorial guard you save in your first fight. You'll be close to full health again. The boss will be pretty weak. Unless you then get a severe case of bad luck. Should be able to just do whatever and win the fight. Of course, can't guarantee that players will try to hoard it. Use it too early, etc. But it is better than nothing and mostly just a 'quick and easy' fix. In my opinion at least.