The question frequently asked about the ST is whether to go west from Florida or east from California. The received opinion seems to be that going west will pit you against constant strong headwinds. They will turn every day into a miserable ordeal like climbing a steep and endless hill. It will stop you in your tracks. You will have to stop for days. Well, the received opinion is not necessarily right. Because I have cycled and camped the ST in its entirety five times from Florida, and twice from FL to El Paso, I know a thing or two on this subject. The fact is these celebrated and vaunted killer head winds may not happen to you at all, but they might happen.
In my crossings on the ST I encountered such west to east winds only once. When that happened they hit me from the side as I went north from Marfa to Van Horn, TX. It was a difficult ride into Van Horn. There I met two fellows from Germany. They were going east. They had been riding those winds for days. To say they were elated and very satisfied with their journey is putting it about right. The three of us got rooms in a small motel. The next morning the wind was gone. It was nearly dead calm. The Deutschlanders were gone. I waited a day or two and continued west into New Mexico, Arizona and San Diego. So sure, it is possible that going east to west will run you into seriously impeding wind. But it is not written in stone and it is not inevitable. Frequently winds come out of the southeast. Many come from the northeast and north. Many days or parts of days there is hardly any wind at all. Cold fronts in winter can bring side winds from the north. Many winds come from north and south, and these affect you the same whether you are traveling west to east or east to west.
Several bicycle journalists recorded strong opposing winds when they cycled west to east on the ST. They recorded them going east to west. If you are planning a cross country ride on the southern tier of states, I think you probably do not have to take the trouble to travel cross country to begin on any given coast because of winds you might encounter. I mean, if you choose a coast to begin your tour based only on wind, I suggest leaving from the coast nearest you. The wind very often does not flow the way people say it does. It is way too variable to predict with certainty.