I'm planning on selling copies of high end pc applications on craigslist which i obtained by certain means(Ar matey.) Can anything go wrong here?

Someone reports you to the appropriate company and you get sued for every fucking cent you have for violating copyright laws?

Yeah, that's a possibility.

Make sure you use something that'll disguise your IP and an email thing that doesn't keep records or something. Also, be on the lookout for any buyer that seems suspicious.

You could try selling to kids at your college.

Copyright get busted and thats tens of thousands of dollars in possible legal fines.