Possible plot holes in first episode of season 2?

Just got done watching the first episode of the second season and there's a few things that aren't adding up.

We learn that Jesse is being extradited to the US to face charges for the hack he was responsible for last season. In exchange for his freedom, he must work for the government to help them locate an abducted 14 year old boy who's being sold on Undacounta, a Silk Road analogue. The plan is to install a backdoor onto the site owners computer by offering an item for sale that he won't be able to resist; the encryption keys to the internal servers of the Parliament.

After posting an ad for the encryption keys the site owner messages Jesse and has him jump through a few hoops. After they complete the tasks and negotiate a price, the site owner throws them a curve ball; he wants to meet Jesse in person because it's too risky to send the keys online. An argument ensues and despite his brother's objections, Jesse agrees to hand over the keys on an infected USB drive.

Okay. Forget the fact that it's not only easier and infinitely safer to send the keys online, what exactly did they need Jessie for? We eventually learn the reason the site owner wants to meet Jesse in person, but that's not until well after he already agreed to purchase the encryption keys. Everything they did could have easily of been accomplished by someone other than Jesse or someone simply posing as him. Plus the whole idea of handing over an infected USB drive, especially to someone as security conscious as our Silk Road admin, is ludicrous; then again the real Silk Road owner wasn't too smart either.

The other thing that makes no sense is the plot with the abducted child. After discovering the true intentions of his captor, he actually manages to escape on a bicycle. Looking for the escaped child while driving around town, the captor sees his bicycle outside of a gas station. The child is asleep on a bench inside (he was drugged) and the attendant, thinking the child is only drunk, is calling the police. The captor however, playing the part of a concerned cousin, is able to talk him out of it.

Now, if you couldn't ride the bicycle to a police station, stop someone on the street, find a phone, or just use the phone at the gas station, wouldn't you at least tell the attendant that you were abducted? It's just a little too convenient that he managed to escape, but not tell anyone that he was abducted.

I certainly enjoyed the first season, which had its faults, I just hope this season doesn't continue in this manner.