I guess I thought I was a smart marketer/musician, but (as always) I still have more to learn.
From this point on I vow never to take money to support my music unless it is officially a gift (which means no-strings-attached) or a loan with a contract. It’s impossible to deal with ambiguities amongst friends, fans, or even companies. Until your band becomes incredibly successful, bartering, haggling and negotiating every dollar at the merch table (or at your office, or at the record store) is the name of the game. Without it, your merch sales will plummet (not that ours are very high).
The guy at your show who only loved the last song but only has $4 isn’t going to go down the street to the ATM for the extra dollar, but if you give it to him for $4 he will wear that shirt everywhere and talk about how cool the guys in your band were. He will evangelize you and generate more fans/sales than the $5 you would have charged for the shirt.
Bottom line is, when I’m dealing with merch and money I either need to know that I answer only to myself/my band or that I have a specific dollar amount I need to reach to not get my knees broken.
If that means I have to write “Monsters are not Myths” in sharpie on a thrift-shore shirt, so be it.
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