Throughout his life he was perfectly fine, some said he was a little overweight, but aside from that he was perfectly healthy.

However, recently, he's been waking up my parents (Im just a 15 year old) in the middle of the night, at like 3am. We're too tired at that point to take him out for another walk, so we let him out into our backyard (it's fairly big and should have enough space if he needs to pee). However when he comes back inside, he is still hyper active. He waits at the foot of the stairs where he is blocked by a gate. Sometimes he manages to use his paws to push the gate aside and run up the stairs to get our attention.

Normally he goes out once in the morning by himself in the backyard.
I take him out when I come home from school at around 5:00 and my parents take him out again at about 10:00 to 11:00.

Now he seems to need to go out:
In the morning
At 2:00
At 6:00-7:00
At 10:00-11:00
And maybe again at night.

He's a little too young for bladder problems isn't he?

Dogs of any age can get a bladder infection, perhaps even more common in puppies. Straining, dribbling a little and then again soon most likely is a bladder infection. Could be something else, even a new noise in the neighborhood at night. Have you made any changes in your routine or his? A good check up at the Vet's might turn up an easy fix.

No, I can't think of anything different in routine. Although lately I have started scratching him underneath the mouth a lot. At first it was just like petting him. But now he craves it. It's like when I sit down, he comes to me and shoves his head directly at my hand so I can scratch the area underneath his neack. He doesn't care so much about the petting, he just wants me to scratch him. Sometimes I wonder if he just wants atttention to be scratched.

Same with his back/rear area. It's weird, sometimes, he just points his butt/rear/back area (I don't know how to describe it but I tihnk you know what I mean) and when I scratch it, his leg goes wild.

Maybe I got him addicted to being scratched in those 2 places?
Well thanks anyway!