Small Cash Trade with a friend

I have a real life friend who has been marked as a scammer, who's selling me a Strange Amby for $2 in real life. Is it possible that I would be marked for this? Would this be considered a high-value/cash trade? I'm trying to get one as soon as possible and he's the only person I know IRL who's available to trade the next day.

I want to buy one with real cash in real life, as I don't have much trading material in TF2(I.E hats I would trade), nor do I have paypal.
Also, why is it wrong to possibly benefit a friend whom I know, even if he has done something wrong? :/

I'm surprised you would even ask that question. He has scammed someone. Someone got cheated because of his actions. If he makes money (real life, paypal, other vritual items) then you are helping him with his crime. As in real life an accessory to a crime is very much punishable for their assistance in commiting, concluding or "getting away" with the crime.

That is why you would get marked for KNOWINGLY trading with a marked scammer (if it was accidental and a small ticket item you would have gotten away with a stern warning, but knowingly doing it is an accessory to the crime).

Aiding and abetting

Just as in the real world, trading with anyone who garners income from illegal sources is facilitating. In other words stand near a toilet, don't be surprised if people say you smell like s✿✿✿ eh?

You mean if I hadn't checked his steamrep, I would not be punished for this trade?
That's rather counter-intuitive but I do get your point there.

And I didn't know he was a scammer until he approached me about the trade, just to add on.

Not really.

Newer players and people who genuinely are not aware of this issue, and not punished, why would they be?

It is actually not easy to get marked for trading with scammers, and those who do so on one occasion are generally given a warning. Only those who willfully trade with scammers after being warned (or being older traders who are known to understand the rules) are in any jeopardy, and even then they generally risk a caution tag. Getting a full scammer tag normally requires continuing to deal with scammers various times with the full knowledge of consequences.

In your case, while I imagine it would be unlikely anything would happen to you for buying a $2 item from a scammer, why on earth would you? You now know why you should not, and that should be an end to it really.

Buying a sandwich from someone who robbed a bank isn't aiding and abetting. In real life, no one would care at all about that transaction.

It would be if he robbed a sandwich bank, you argument is specious.

He robs the bank, uses that money to buy sandwiches to sell to you. Your happy you got a sandwich but he is happy because robbing the bank paid off for him when you bought the sandwich. Would you have still bought the sandwich if you knew how he got it? Not all immoral decisions are crimes in real life but they are still immoral.