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[SanDiego]

Also, I have rather strong hair (roughly 106 microns (...)

How on Earth do you know that? 

During my biophysics class on med school one of our assignments was to measure our hair under microscope. Don't ask me why.

I had a period when I deciced to have long hair. Also, I have rather strong hair (roughly 106 microns, while average male has ~96 microns).

(Literally, my dad tried to use an electric razor on it, and my hair broke the razor somehow. It destroyed 3 of the things until he used scissors.)

I broke three brushes in my hair.

[Aptus]

I used to have long hair and for me it was pretty easy keeping it straight with just a comb and only washing the hair every other day. My biggest issue was GETTING long hair because my hair possesses the power of anti-gravity. I have like natural guido hair making it stand straight fucking up until it gets pretty damn long (as in if I just grow a few cm of hair it will stand straight the fuck up and it is uncanny as hell). I've been thinking about growing my hair out again but I just wish I could skip that middle step :p

[acetech09]

And also, you don't have to have neatly combed hair...

http://youtu.be/tEVUpeh_cF8?t=25s

[Vector]

Long hair. . . boar brush, and slowly work out knots from the bottom up to the top, working in sections.  Also, shampoo + conditioner.

I cut my own hair in such a way that it's easy to take care of.  Mostly I make sure that it's all really really flat and none of it is crossed when I wash it, and that it's also all pulled back from my face.  Then when it dries it'll remain back from my face and the layering will look good.

[mastahcheese]

I broke three brushes in my hair.

just regular brushes? I gave up on those worthless things years ago. I have to use one of those heavy duty afro picks to comb it. I just completely gave up and stayed with short hair because it's too much of a hassle.

[Max White]

By unwilling to use any chemicals, does that include shampoo and conditioner? Because those are important.
If you are using them both, you might be using them too often. Shampoo washed the oil out of your hair, and while too much of it is bad, too little will make your hair dry and look all scraggly.

[Neonivek]

I use Shampoo but not Conditioner (but have nothing against conditioner)

I just don't use either Moose or Hairsprey because I hate the way it makes me feel... Icky gooey sticky hair...

[LordBucket]

I use Shampoo but not Conditioner

Try using conditioner then. Be sure it's in separate bottles. Ask any girl you know for a recommendation, though you might have to go through a couple different brands before you find one you like. The procedure is: wash with shampoo, rinse it all out, then rub in conditioner while your hair is still wet, then let it sit for a while. Brush your teeth in the shower or something or wash something else for a few minutes, then rinse it out.

It's not as important if you have short hair, but it should generally make your hair nicer and more manageable.

Be aware that once you take enough steps down this path it may be difficult to go back. Not using conditioner after getting used to using conditioner is like trying to go without toothpaste.