If I try to get something for a tenant after planting a doghouse, the dog will chase the deliveryman and fail to plant anything else.

Worse, the deliveryman will enter a loop, still trying to delver whatever I wanted planted, and freeze anything else that needs planting.

Is there a way to solve this?

Yup, use a foreman to get rid of the dog kennel. When that's done, the delivery man can finish the delivery no problem. Alternatively, you could build a Fun House and use a clown to distract the dog or use a gangster (armed with a firearm) to kill the dog. If you kill the dog with the gangster, the dog will come back after a certain amount of time has passed. The latter 2 methods are more trouble than it's worth though, so just nuke the kennel with the foreman, let the delivery man deliver the stuff and replace the kennel afterwards.

Keep in mind when adding gadget factory stuff to a property, ALWAYS place a dog kennel last and you know you are never going to add any more stuff to that property.

As far as I remember you have to place the house so that it's possible to place the dog house in what's the backyard to avoid having the dog attack the deliveryman, try it out.