He does look like he's gained a little weight, but it's definitely slow. Giving him one big grain meal a day can be counterproductive. Strategy (& probably the Nutrena pellets... not sure exactly which one that is) is very high in NSC (sugar/starch) which horses don't process well. When you feed a lot of it at once, it gets through the small intestine undigested (and very acidic!) and results in hindgut ulcers.
If you can't feed in 2 meals (3 or more would be even better) then you might consider dumping the Nutrena & Strategy and switching to grain free alternatives- soaked beet pulp, rice bran, alfalfa hay/cubes/pellets, and/or oil (flaxseed if you can get it, canola if not). It's still ideal to feed these in at least 2 meals, but at least you won't be getting the influx of sugar/starch. Since the hay in your area is on the poor side, I'd also consider adding a ration balancer or multivitamin in to the mix.