这类小文很有意思。你花的功夫不少啊!

fantasying how everyone would fawn upon me and scramble to ride on my coattails if I could hit the jackpot or rise to fame someday.

May be better this way:

fantasying everyone was fawning upon me and scrambling to ride on my coattails after I  hit the jackpot...

Thanks for posting a nice piece of writing for us to learn and enjoy Slangs.