Sorry man, but the Sam & Max items are notoriously pricey. Let's put it this way, people routinely pay $30 for Big Kills because of the rarity of the Sam & Max set, and you can't even get a NV one via Poker Night like you can a Lugermorph. (Technically they're all NV.)
Pretty much the most in-demand, rarest Vintage hats scrounge to hit $10 apiece.
So if you want a Big Kill, yeah, you're going to have to put some serious items up for trade. Your Stainless Pot is Level 100, so that's a good start. Your Vintage Fedora, or your Detective Noir if you don't want to part with that. Also, your Milkman and V. Professional's Panama have doubled number levels, that helps their value, but I don't think people care about the Panama that much. Still, if you threw, say your Pot, your Panama, and your Noir into a trade, you might get one.
It helps if you post up on
TF2TP too, and be patient, sometimes people will trade for less if the right hat is involved. Like I said, that Stainless Pot Level 100 is a solid start, in fact you might even just stick that up on TF2TP and see what offers you get.