Sometimes I Am Envious of You
And by "You" I mean anyone who plays with just a ruleset and an oracle (such as the solorpg tool). I've read several actual plays using this method and it appears the games move fast, do not get bogged down, and the players don't fret over whether or not their choices are too simplistic.

While I certainly use an oracle in my games, I'm too concerned that by only using an oracle my questions and interpretation will steer a story in the direction I want it to go instead of, as with a real GM, presenting unknown situations that I have to react to as a player. To that end, I have lists and lists of tables and generators that I can consult to randomize as much as possible. Furthermore, I'm always thinking about how to handle certain situations that might occur in my games. No joke, I have actually put a lot of mental time mulling how to handle challenges I expect to occur in my games, even going so far as to document the rules and create necessary tables, only to have the event never happen.

I good example of how I develop a system instead of relying on an oracle roll is the chase scene in Chapter 10 of my Kage Gordain campaign. Using just the oracle I could have simply compared Sylralei's and the Pirate's speed stat, factor in any other variables, such as how much head start Syl had and her familiarity with the caves, and come up with a Likely Odds. Then using those odds, ask a question like, "Does Syl escape from the pirates?"  Instead, I felt the need to develop a point system where each party had to make a Speed roll to earn points. If the pirates' points ever equaled Syl's she would be caught. Furthermore, I factored in a head start for Syl, decided how many rounds the chase would last, and occasionally introduced events that might give either party an advantage or disadvantage on their roll. Much more involved than one simple question.

It's easy to see how this method can really bog down gameplay at times. However, before you think I am complaining, I don't really mind. I love tables, the idea of randomness in a game, and exploring different systems or coming up with my own. Sometimes, when I find a new tool, I roll a few results on it for no other reason than just to see what comes up. Using the above example, the chase was much more exciting using my system and it would have been with a yes/no question. That is what I find interesting and exciting and is one of the reasons I enjoy free-form solo role-playing a little more than gamebooks and adventures written for a solo player (such as Fighting Fantasy).

I just wanted to put this out there and see if anyone wanted to share their preferences and experiences of using oracles and other tools.
Your chase mechanic sounds awesome and I agree that a simple yes/no is less exciting. For example,
"Do I complete the quest?"

So while there are extremes, there are also many middle-ground solutions. With the chase, for example, "Are the pirates catching up in this round?", "Do I have an opportunity to hide?", and things like that.

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