Resonance Hybrids

Hi! I'm self-teaching and reviewing some organic chem using the Klein textbook. I'm really happy with it. Currently going through resonance hybrids. I felt like I had this down, but then I tried this problem and the solutions manual doesn't show my 4th resonance structure. This is actually the second problem where I've drawn an extra structure that wasn't in the solution and I can't for the life of me figure out what I'm doing wrong.

My attempt: From the 3rd structure, I have an allylic lone pair that I'm turning to a pi bond and then having that pi bond turn into a lone pair on the neighboring carbon. I haven't been able to see anything preventing me from doing this. I even thought about sp2 vs sp3 hybridization and if that lone pair on the oxygen was actually able to participate in resonance. From what I understand, the lone pair has to occupy a p orbital. This is about the only reason I can think of as to why my last structure isn't valid. The oxygen is sp3 hybridized, so each lone pair occupies a hybridized sp3 orbital, and therefore there is no p orbital conduit for the lone pair to move through to actually generate the resonance structure. And just to make sure, that neighboring carbon that possesses the double bond, does in fact have a p orbital that can participate in resonance, right?
Am I off base with what I'm saying here? Is there any other explanation I'm just completely overlooking?