I only given an answer to the first question. My answer is an addition to the answer given by janmarqz. Basically I just provide some plots for his second point.
Visualization
I like the visualization given in V. Arnolds, Mathematical Methods of Classical Mechanics.
Suppose we have a covector $\omega \in T^*_0\mathbb{R}^2$, we then draw the hyperplanes $\dots, \omega^{-1}(\{-1\}),\omega^{-1}(\{0\}),\omega^{-1}(\{1\}), \omega^{-1}(\{2\}), \dots$
(Let's call them the contour lines of $\omega$.)
If we now want to see how the covector acts on a vector $\mathbf{v} \in T_0\mathbb{R}^2$, we just draw the arrow representing $\mathbf v$ and look how many contour lines we hit.
Below I have drawn this method for a basis $\{\omega, \eta\}$ of $T^*_0\mathbb{R}^2$.

Why don't we draw arrows for covectors?
A typical difference between tangent vectors and cotangent vectors is their transformation behavior!
Let's use the linear transformation $\Phi:\mathbb R^2 \to \mathbb R^2: (x,y)^T \mapsto (x,2 y)^T$.
Vectors transform via the differential $T\Phi: T \mathbb R^2 \to T \mathbb R^2$ (sometimes also denoted by $D\Phi$). In our case this is just the Jacobian of $\Phi$ i.e.
$\mathbf v \mapsto \begin{pmatrix}1&0\\0 & 2\end{pmatrix} \mathbf v$.
Covectors transform differently! An example is the gradient of a smooth function $f:\mathbb R^2 \to\mathbb R$. In classical calculus, we have see, that $\nabla f$ is always orthogonal to the contour-lines of $f$! But if you apply the transformation $\Phi$ and transform $\nabla f$ like a vector, it will not be orthogonal anymore!

But, if we visualise covectors by their contour-lines, they behave correctly! For example, if we draw the contour-lines of $df$, they will stay tangent to the contour-lines of $f$ after applying a transformation to the visualization, which is the correct behavior!
This is one of the reasons, why we treat vectors and covectors differently. And also the reason why we draw contour-lines of covectors instead of arrows.
Higher Dimensions
The reasoning above is still valid in higher dimensions, here the contour-lines become hyperplanes instead. (The example with the gradient is only plausible for Riemannian manifolds, but the example should just give a feeling how covectors are different than vectors. In general covectors transform according to the inverse of the adjoint of $T\Phi$, i.e. $\omega \mapsto ((T\Phi)^*)^{-1}$. )