You are, of course, entitled to your opinion. I have no idea where the money goes - probably into some guy's pocket, as you say. At the end of the day though, you're buying clothes, it's not like you're being scammed - you get a tangible item for your cpin, just like if you buy a scarf from a vendor outside the stadium.
The club's too PC nowadays. There was once a time when the official merchandise often featured the Union Jack. Nowadays it's seemingly offensive, maybe due to the independence movement or supposed sectarian connotations. However, I preferred it when the club was unashamedly British.