Yes. Yes. No. No

Is it east or west of I-25?
Is it I-25?
Is it an interstate?

west of I25
not I25
not an interstate

US Highway?
Does it run north to south, or east to west, or is it diagonal?

State highway, north to south

How many digits does the highway have? Is it single, double, or triple?

single

1?

hehehehe... no

Colorado Highway 2?

Found it. Hwy 9 north of Breckenridge, looking north.
http://goo.gl/maps/bc6jq

Somewhere between Gold Hill Road and Jarette Dr.

Aced it!
You're up!

I'm thinking this will be easy, but maybe it won't be.

Oahu, east coast?

yes

Kamehameha highway?

yes, but where.

is it closer to kahuku or ka'a'awa?

ka'a'awa

in what direction from there?

north of Kaaawa

found it
http://goo.gl/maps/C75Hu

That's it! I used to live in Hawaii, and that area was one of my favorite parts of Kamehameha Hwy.
Your turn.

this is at an intersection, so you'll have to find both roads. there's a hint buried somewhere in the picture also.

That's Coors Field in Denver, pictured at the intersection of Park Ave W, 22nd St, Delgany St, and Wewatta St. XD

Don't test my knowledge of ballparks!