BMOC & Ebenezer | Not tradable become tradable?

Sharking much?

If it says not tradable on the hats they will never be tradable.

In F2P, all things that you get from trade are tradeable to other users. BUT some items directly say "No Tradeable", so it's completely no. You should check the TF2 official wiki.

Yes they will be tradable. Trust me ALL F2P items (Except that one donated by other users) are not tradable for the F2P Player untile he buy the Upgrade Pack or Orange box :)

Yes.

He doesn't need to buy the Orange Box. He can buy a weapon on Mann Co Store (with a 25% discount if he select "Try first").