I think contest rewards should be more than a few hundred cash and pizza, especially since 500-600 cash is at most best for small upgrades or sc academy things when you're not that far along in the game play. There is honestly no incentive to get the leaderboard perks when they are small and well don't amount to anything if we binge hard in a gym for the current lb rewards. Giving a larger sum of cash/pizza will drive more people to fight for the leaderboard, and it could either boost a small player or help a larger player get that extra stretch of cash they need for the next upgrade.
Head to head rewards are upgradable in the academy if that’s the contest you’re asking about — the biggest reward on them is the roomie power up ticket tho imo and that doesn’t upgrade; at least through lvl3. The speeds get better as you tier it up
Yes. Daily Contests (Daily Room, Daily City, Daily Roomies, Daily To-Do List), Head-to-Head Contests, and Everyday Errands can all be researched in SC Academy for better rewards. Daily Contests have 4 Levels Head-to-Head Contests have 4 Levels Everyday Errands have 7 Levels To give you a picture of how the rewards (both Star Rewards and Leaderboard Rewards) increase from one level to the next, let's take an example the current Head to Head, "Treat Yo'Self." Below is a comparison of its Level 1 and Level 2 rewards: Levels 3 and 4 are even sweeter. All you have to do is upgrade them in SC Academy under Home Grown.
That research upgrade cost can always be recovered as it is a one-time thing. Daily Contests happen daily, Head-to-Head Contests happen every 4 hours, and Everyday Errands every 6 hours.