Texturing problem need help

ok so I am a noob and don’t really understand the basics of doing things have played around with modeling and want to texture some of my models. I can change colors of selected surfaces. But I am creating a Neighborhood type map that my character will navigate through. However I want to use Multiple images for things like grass, Road, Sidewalks. I can’t seem to get the textures I create with images to appear on the part of the 32x32 grid that I make. Also I am perplexed by scale in blender is 32x32 big enough for this or should I go bigger or smaller? Is there an image size that the texture has to be in order for this to work.

I want the texture to fit in a 2x2 Square somewhere in the middle and at the bottom of the 32x32 grid. and repeat every 2x2 section until it gets to the top of the 32x32 grid

Can you post some screenshots or the .blend?

This I what it looks like before I texture it. I want the highlighted part to have a road texture from an image I downloaded.

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This is with draw type Shaded. I have been looking at it from draw type Textured. Maybe I am not understanding the difference between Texture and Shading( can someone explain?). How do i confine shading to selected area in img 2(before.jpg)? oh and I want shading to be smaller so the white line takes up a 2x2 area. to simulate a dotted residential street.

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This is in draw type Textured. For those who are interested.

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Use different material indexes, make multiple materials and push the ‘assign’ button to selected faces, 2.49 can have 16 materials per object. (2.5 can have around 32,000 materials per object)

Then use UVmapping to fit the texture to the faces.

Thanks for the info everyone. I have figured it out.