I am attempting to make a large night map, and I am using the lit street light model, but I can not get the light to shine correctly in the open. If I place a light against a building with a lamp It looks correct, but the taller street lights out in the open dont light realistically or the light doesnt reach far enough to touch the ground. The only difference I see is that my hands and gun become lit when standing within the light radius. Any help appreciated.

You can go with one of two lighting options: a light source (the spherical method) or a spotlight.

The light source assumes that the light bulb is radiating in a circular pattern with solid objects obstructing the sphere's reach where applicable. This is what you're already doing. You can tweak the effect of this by adjusting the position of the light source (the entity that gives off light) and the light model (the lightpost).

The other lighting method, the spotlight, requires the light source to be connected to an info_null entity. Basically, this means your light is "looking" at the info_null spot. There are even properties you can assign to it. Open up your mp_matmata map to see how spotlights work.