Hi Jonny. Your beautiful senior Spooky sounds so precious. As with humans, the seniors do so much rely on our help as they grow older. Perhaps you could discuss again with your vet the possibility of a dental cleaning/? Of course, the medical conditions you mentioned do pose some risks. But, the anesthesia used now for dental cleanings is quite "light." I think, as others have said, that crushing dry food in with the wet might help. I would also suggest giving him smaller, frequent meals, instead of a greater amount at any one time to reduce the risk of vomiting. Please give your Spooky a hug and kiss from me. You're a very caring parent