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I am sorry you are having these problems. Skin disease is really common in dogs and there are many things that can cause it. Allergies are very common and these can be allergies to things in the environment such as pollen, grass, tress etc and these types of allergies will show a seasonal variation with some types of pollens/plants being in bloom at different times of the year. Often the skin is made worse by the development of secondary infections with yeast or bacteria. The main points to address are to make the diagnosis (can be done by simple examination/response to treatment but sometimes other conditions need to be ruled out such as mite infestation (demodex/sarcoptes) using skin scrapes. Blood tests can be done to look for allergies too) if infection is present then this needs to be treated and if an allergy is also present then the bodies response to these allergens needs to be managed. This can be done in a variety of ways and antihistamines are a great, simple, cheap and safe way to manage allergies, just like humans with hayfever. Antihistamines can be given throughout the year. Sometimes if the allergy is overwhelming then other more potent drugs can be used to manage itch and skin reddening, a great one that we have recently started using is called apoquel. So as you find that Wilson is great for most of the year on antihistamines, the occasional use of apoquel may be helpful in times of extreme allergy such as now. This is not cheap but is very safe and effective. It is worth remembering that allergic skin disease cannot be cured, it is a life long problem which requires continued management.
It is also helpful to keep the skin in good condition and the use of supplements such a omega oils (nutramega, yumega) can be really helpful.
So it does sound as though Wilson has allergic skin disease, and it is great he is managed so well for most of the year, but flare ups do occur and a short spell of a stronger 'anti-itch' medication such as apoquel may be needed.