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One of the projects I'm working on is a getting pretty lengthy at this point. It's not necessarily hard, but it will take a solid chunk of time for the reader to get through it. 

Everything as a whole doesn't take itself that seriously, so the endings scattered around aren't really meant to feel like losing either. The main challenge will be: figuring out how to get a high score. There's also some occasional variable features involved, but they're pretty easy to understand.

I was wondering: how do people weigh things like story length, basic variable features, and scoring systems into the overall difficulty? I want to make sure I get the story difficulty accurate on it, so it doesn't seem easier or harder than expected to get through.

The difficulty rating is kinda useless, imo. A story's difficulty is really open to interpretation and is slightly different for every player. I choose my difficulty rating based on how hard the decisions are to make, others base it on the difficulty of the puzzles.

The best way to decipher how difficult your story is is to have beta testers play it first and ask them, then round it up as best you can.

Good thought. I'll try not to overthink it then. When it's finished, I'll ask the testers how difficult they think it is. Or when in doubt, I'll just default to a 4/8 and call it close enough.

The best way to determine your difficulty is not to. Nobody really reads it or gives a damn. Just make it as difficult as you can and give it a 1, then people might actually pay attention to it.

Losing endings don't bother me, the only time I notice 'difficulty' it's when the author seems to be going to great lengths and setting up a bunch of looping scenarios to keep the player from getting at an end game link.

In that case I'm more likely to just stop playing than bother to finish and complain about it, though.

I appreciate the responses from you all. I'm probably just overthinking it too much (bad habit of mine!). Mainly trying to get the experience as clean as possible for people who check it out. Sounds like it's not that big of a deal, so I'll set it to somewhere in the middle and call it good enough. It wont be hard, but it'll take time to read through the main path, and some effort to get a higher score.

And yeah, I'm not a fan of endless looping/resets that pressure the player into certain choices, rather than let you end it at places you naturally lose at. I don't plan to ever do something like that; an ending is the end. If people want to try again, they can start over or continue from their last save point.

I just tend to rate the difficulty based on how many times you can die in the story. Typically the longer the story, the more times you can die, so I end up giving them the highest difficulty rating even if it isn't technically all that difficult to get a good ending if you're persistent enough.