Screwing up his uncle's instructions.

What the hell? He never heard of an uncle Marcus or whatever. Now he was expected to suddenly believe he had an uncle Marcus with magical powers?
No doubt this was some kinda scam. Perhaps Timothy wasn't the image of a straigh A kid, but if it was something he had it was street smarts.
He was probably expected to believe that giving the dollar to the delivery girl would prove that it worked if it works. Well that makes sense, except the delivery girl was probably in on the scam, would do one thing he asks of her for a dollar and expect to see Timothy all impressed.

Looks like Timothy had it all figured out, except for one thing.
They want to rip him off right? Rip him off,,, of what? All the debt he has? A room in his dad's basement?

Timothy considered if this was a ****.
His parents didn't exactly have dough to spart. They did, however, have kids to spare.

They did all this effort to plan and organize this scheme, all so they can pull a fast one on the shittiest piece of shit in the neighbourhood? Possibly in the county?
Timothy wasn't sure what was going on. He knew one thing, and one thing only; scam or no scma, getting command over the cute girl in front of him wouldn't be half bad.

Timotthy tore open the smaller envelope with his index finger and flipped it over, a single circle of brilliant metal fell into his hand, large enough to take up about his entire palm.
He took a look at the medal he had allegedly inherited.
It depicts a fancy looking middle aged woman in profile with the words "liberty" spelled in capital letters in an arc above her head. Between the letters E and R a small hole had been drilled and a piece of string tied together to form a necklace.

"Know what?" Timothy said proudly with a smile, "You've done such a good job! I'm impressed, by your professionalism, and your courtesy! You know what you deserve if anyone deserve it?"Timothy waved the bill like a flag as he pinched it between his thumb and middle finger, "A whole dollar tip."
"Thank you sir," the delivery girl responded with a giddy smile holding the clipboard, "But my only reward is a work well done and the satisfied smile of our customers!"
"Oh, come on! Don't tell me you couldn't use a good old tip, little missy? Just take it and continue the good work you're doing."
The delivery girl was still smiling, but her smile was worn thin with patience, "Sir will, of course, realize he was reading his letter out loud."

Timothy's face drained of colour and he stopped waving the bill. He breathed in through his teeth.
"Of... of course," Timothy said trying and failing to save face, "I was just gonna give you the tip regardless, really."
The delivery girl's smile didn't fade, but her eyes was filled with irritation. "As if you ever gave a tip in your life," The delivery girl finally said, "Look, I don't know what kind of voodoo magic trick your dead uncle had planned for you, but don't count on me to be part of that. All I need you to do now is sign that you've recieved this delivery, all right?" the sassy girl inside having burst through, she extended the clipboard in one hand and a ballpoint pencil in the other.
Timothy sighed. This was one hell of an actor for sure. If he had an uncle Magnus he sure hoped he wasn't watching from heaven right now.