Thanks a lot for playing and for the detailed feedback! That's actually really valuable to hear.
I just updated the web build, and I'll upload a new downloadable build later today. One of the changes is a star rating (1–5) for each jump phase to give better feedback on what went well and what didn't.
The game also has quite a bit of intentional randomness at the moment. Wind direction matters—a right-to-left wind gives you lift, while the opposite pushes you down—and gusts make jumps unpredictable(sometimes there are none sometime 4 in a second). The best glide comes from keeping the wheelchair level while getting a favorable wind.
The game mechanics, items, and contracts are still very much WIP, and I agree the game can feel a bit unfair right now. Even as the developer, I only manage to consistently sweep all three wins and longest jumps in about 6 out of 10 runs. Balancing and making the mechanics easier to read is one of my main priorities.