Yeah. Firstly, how much tailoring skill does it take to produce a tie-dyed T-shirt?
Secondly, the numbers. This is the huge problem. Firstly, other than Fashion Designers, Sweatshop Workers would be the most logical choice for candidates for this. BUT... the average tailoring skill for these guys is 2-3. (I think musicians and such have similiar). 4 and higher is pretty exceptional. In other words, most people would expect 2-3 tailoring to be sufficient to make money, right? ... WRONG. The average sweatshop worker loses you money here? You have to be a fashion designer or elite tailor to make a decent tie-dyed t-shirt?
Secondly, there must be something wrong with the buy and sell prices for those shirts and materials! Even with like 7 tailoring, it's something like 300 in costs and 350 in sales... er. WTF. The profit margin on these things is like 900% in real life, not 10%. (you probably expect to pay $5 for something that cost 50c in materials... most of the cost is probably labour and stuff)
Also, real life T-shirt sellers can make quite decent livings. Selling clothes should be LCS most profitable business, not it's least profitable one. (artists, admittedly, are well known to make it hard to make ends meet and do it for love of art, not profit)
Third problem is that you don't realise you are losing money usually until the end of the month, (cause your cash might go up from donations+music) and if you had multiple workers assigned you can only guess which ones were losing money and which were making.