Yeah your garage is in a hole. It looks like the natural path of the land is to drain toward the back right side of your land (facing the garage) so if it were me I'd start there. Get that skid steer and cut a path about 10' wide on both sides and back of the garage and give that water a way to flow toward the back end of your property.
Then I'd cut a little dip about 2" deep and 4' wide all around that parking lot pad in front of the garage so that the concrete is higher than the surrounding dirt. That sucker is just going to funnel water into your garage.
You got a lot of work ahead of you, but I'd say two weekends could do it. That's sandy dirt. Fun to work in and easier by a WHOLE LOT than OKC area clay.
Then I'd cut a little dip about 2" deep and 4' wide all around that parking lot pad in front of the garage so that the concrete is higher than the surrounding dirt. That sucker is just going to funnel water into your garage.
You got a lot of work ahead of you, but I'd say two weekends could do it. That's sandy dirt. Fun to work in and easier by a WHOLE LOT than OKC area clay.