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Hello and welcome. The expert you were looking for is no longer in the dog category . It sounds like your pup may have airborne allergies which seem to be particularly bad this year and I suspect that is why the dog is taking Bendryl and is on steroids.
Depending on when the dog got the steroid shot , you may want to talk you your vet about Apoquel. This seems to block the need to scratch and it can work within two days, though you do need to give it twice a day for longer during the season that affects the dog.
I was in the same spot you are now and I requested this for my dog. No more benadryl needed and she has been itch free for four weeks now.
Here is more on this drug. https://www.zoetisus.com/bmst-minisite-apoquel/index.aspx
Apoquel has been compared to another popular drug call atopica and the newer apoquel has been shown to be a better fit for most dogs. But do discuss both with your Vet.