ya mystery series with puzzles throughout. Rich millionaire creates the games and invites multiple people to participate for a prize. Read around 2016

[Will]

Pretty sure title includes the main characters name. In one of the books there is a glass bottle left under a tire giving the car a flat tire.

[One-Sentence]

The Westing Game by Ellen Raskin?

https://www.goodreads.com/book/show/902

[Jessica (Goldenfurpro)]

Maybe Escape from Mr. Lemoncello's Library?