Thanks to DwarvenDervish's suggestions, I decided to try shrinking down normal trees for the Overland map in order to keep it a seasonal look, and it's looking very good. I am now very pleased with how the Overland map is coming out.
This is a tilted view from Silverymoon looking toward Silverymoon Pass in the Nether Mountains.
I changed up the texturing and you can see this is looking very good. I am also very impressed with the way the Silverymoon Pass came out. I used a little brown and orange coloring on the textures to make the mountainside and "broken" land of the pass come out.
On top of that the area around silverymoon now look very authentically Autumn. I probably could do a better job with the textures, but I think this will do for an overland map.
On to the Moonwoods.
Basically each part of the Moonwood I'm making are going to have a slightly different forested look as in the above example. This is the place around One Stone and the Sky Pony camp. These two points are map locations. The one to the right is One Stone, the one to the left is Dragon's Heart, both of which you've seen in previous areas I've designed.
In this specific area I've been able to match the textures to those I used in that specific location. And it's turning out really well. When this map comes out it's going to be a very subtle blend of one environment into another, into another.
As in the example of a completely different texture pattern around Quaervarr in the Southern end of the Moonwoods.
You'll notice older areas of my Blog I showed Quaervarr and the screenshots of what the area looks like. Well this was no exception. I've mapped the texture pattern as close as possible to Quaervarr so it will seem a smooth transition when you enter the town.
Keep in mind this will have Tree coverings I left out so you could see the texture job.
Admittedly though I am having to squeeze and get really creative with textures, because you're only limited to 6 textures in any 4 square area, and sometimes to get the environments correct I'd need a good 8 because of the blending from one environment to another.
To close... it is an intricate job, as you can see I have more of the Overland map done, but it's still not a large amount.
But if you want to do it right... it is an intricate thing.