I think point 2 could be an advantage, not a downside. If no-one you speak to mentions the broken window, maybe it's not a big issue. This assumes you speak to a mix of old and new users
- Twitch is losing money because the costs of running the platform are higher then the revenue
- Twitch is losing money because they're aggressively investing in growth
if you want to know about the viability of the concept, I'm not sure which one it is, video streaming and small payment processing could both be quite costly
While I agree with your sentiment: most people who DON’T follow the advice will propably not ship anything either as shipping is hard and rare in any case.
and the second version compresses better, as my intuition already thought, without knowing how gzip works, because you still need a kind of identifier for repeated strings, and how much shorter than 1 byte can they be.