I hired and beat this game not too long ago.
Night #1: Classic Era Stages
Day #1 + Night #2: Classic Era Challenges + Dreamcast Era Stages + 1/2 Dreamcast Era Challenges
Day #2 + Night #3: 1/2 Dreamcast Era Challenges + Modern Era Everything + 1/2 Red Rings + Final Boss
Day #3: 1/2 Red Rings + All Extra Trophies (hardest one was 'Cant Touch This'; defeat final boss without being hit.)
There's a total of 50 trophies in the game, got me from Level 1 Trophies to Level 4
Really fun. Some of the trophies were pretty clever, like beating Chemical Plant Act 2 without touching the water. It was tricky, you needed to go the right route and time jumps.
Recommend to everybody who likes fun.
Also. I had trouble with the Act 1 Rooftop Run Race & Act 1 Wisp Planet, because they took me about an hour each. The strategy needed is spin dash like the fucking wind. And take all shortcuts possible. And don't glitch into the fucking level all the fucking time and run around on invisible platforms. I did glitch into the ramps a lot, the curve ones, for a person who likes to boost a lot, boosting on a curve ramp makes you get stuck and run around inside the level.