I don’t find Mr Imma hard to craft/shop for at all! But his wishes are simple. He doesn’t mind getting the same type of gifts every year.
I try to make a new pair of flannel PJ/lounge pants every year for Christmas. He likes stuff related to his team or WWII history. He likes craft beers, especially ones that are hard to find. I repaired some underwear for him a while back, I used some novelty print fabric I had lying around and he still cracks up every time he sees those. So I think homemade underwear is going to be a new Christmas tradition.
He also gets a lot of beer gifts and they often come in those rustic looking wooden crates that hold 6 bottles. I set those aside and when we need a gift for another beer lover we just fill them with new bottles. I made liqueur last year for a friend and her husband Speculaas cream liqueur . My brother is into all sorts of fandoms so I just make something related to what he’s currently into. I helped him move the other day so I’m pretty sure he appreciates homemade, he’s kept them all!