Want to add my opinion.
The increasing of the price because of better blanks is acceptable (and actually it's great that you bring new blanks), but the thing with shipping looks like strange decision. I'm not a specialist, but, in my opinion, for usual customer it looks like a motivation to buy less... a lot less.
As I understand, shirt.woot is not on its peak and it suffers from small amount of customers/sales (in comparison with previous years). But does decision like that would solve the problem? Because it looks like a lot of people would not buy several t-shirts as one purchase, they would buy just one and almost always only on side sales and not from the catalog. Shirt.Woot is known among buyers like a great place for buying a lot of t-shirts per one purchase, but after the change it's not a great deal.
Maybe it would be a good idea to add some scaling price system (the more you buy - the less you pay per one t-shirt)? Or some additional discounts if you buy a lot of t-shirts.
Or maybe use the previous system but with a little increased price of t-shirts and a little increased price of shipment for all order. I mean, it's possible to find some variant in between.
About making catalog t-shirts $19: it looks like it would bring sales amounts from catalog almost to zero, I mean that's definitely too much for most customers, and buyer should really-really want that shirt to buy it for that price.
I understand that those decisions were made by professionals (and the change of price was needed) and were economically justified, but still... as for now it looks like it would decrease even already small (in comparison to better times) amount of wooters.
I understand that we don't know all the factors you know (I mean, Woot staff) and I hope that you'll figure out how to improve Woot and get it to its previous glory or better new one