When thinking about plants to group into guilds, it is important to consider the habits of the plants.
In your list, you have apple trees, which come in full size, semi-dwarf and dwarf sizes - which size tree you choose will matter as to what you might plant with it.
Pumpkins - and pretty much any of the squash or melon families - are broad leafed spreading vines that will climb your tree and will smother low growing plants in their vicinity. They can and will climb your trees, which probably is not good for fruiting trees that can strain their branches with the weight of their own fruit production, without adding many pounds of squash vine!
Tomatoes are sun demanding plants, they are not going to appreciate being shaded, so placement near trees has to be carefully considered for where the tree's shade falls. The tomatoes and the pumpkins might not get along well, as the pumpkin is likely to try and climb the tomato. In fact, I have squash that have reached across several feet of open ground and are trying to climb some of my tomatoes right now
Asparagus is a perennial, while the pumpkins and tomatoes are annuals. I think the tomatoes and asparagus are probably reasonably compatible, at least in terms of their growth habits. You will need to keep the asparagus well marked, so that you don't start digging up your asparagus accidentally. It also takes about three years before you can start harvesting asparagus.
Comfrey will be fine around the apple trees, attracts pollinators, great dynamic accumulator for chop and drop. Which is why it might not be a great choice for putting in among tomatoes and asparagus, when you are going to want to be able to easily cut back the comfrey. Comfrey once established could probably hold its own with the pumpkins.
Oregano is likely to have some trouble being overhwelmed by pumpkin, but should be ok around tomatoes and/or asparagus.