In the end, this is just a simple case of computing a tangent map and the fact that $\pi:TTM\to TM$ defines a second vector bundle structure on $TTM$ is not relevant for the problem at hand. (Partially things also get a bit complicated because you are using a notation that makes it complicated to distinguish between and object and its expression in local coordinates.)
Just start by thinking about how one constructs charts on the tangent bundle $TM$: You start with an open subset $U\subset M$ and a diffeomorphism from $U$ to an open subset $V\subset\mathbb R^n$, whose components are the local coordinates $x^i$. Denoting by $p:TM\to M$ the canonical projection, you get an induced diffeomorphism $p^{-1}(U)\to V\times\mathbb R^n$ that is used as a chart on $TM$. The first $n$ components of this are just the local coordinates $x^i$ and if you go through the construction, you see that indeed the tangent vector with coordinates $(x^1,\dots,x^n,\xi^1,\dots,\xi^n)$ exactly is $\sum_i\xi^i\tfrac{\partial}{\partial x^i}|_x$ where $x$ is the point with coordinates $x^i$. Now this shows that $(x^i,\xi^i)$ is a local coordinate system on $p^{-1}(U)\subset TM$, and hence given a point $\xi_x\in p^{-1}(U)$, any tangent vector at that point can be written as $\sum\alpha^i \tfrac{\partial}{\partial x^i}|_{\xi_x}+\sum_j\beta^j\tfrac{\partial}{\partial \xi^j}|_{\xi_x}$ for real numbers $\alpha^i$ and $\beta^j$.
At this point, it is best to forget about vector bundle structures and all that and just notice that $\pi:TTM\to TM$ is the tangent map (i.e. the derivative) of $p:TM\to M$. Since $p$ maps $p^{-1}(U)$ to $U$, this tangent map maps $Tp^{-1}(U)$ to $TU$ and hence can be expressed in the local coordinates we have constructed. But in these local coordinates, we simply get $p(x^1,\dots,x^n,\xi^1,\dots,\xi^n)=(x^1,\dots,x^n)$. This readily shows that the tangent map sends $\tfrac{\partial}{\partial x^i}$ to $\tfrac{\partial}{\partial x^i}$ and $\tfrac{\partial}{\partial \xi^j}$ to zero. Otherwise put,
$$\pi\left(\sum_i\alpha^i \frac{\partial}{\partial x^i}|_{\xi_x}+\sum_j\beta^j\frac{\partial}{\partial \xi^j}|_{\xi_x}\right)=\sum_i\alpha^i \frac{\partial}{\partial x^i}|_x$$
and this equals $\xi_x$ if and only if $\alpha^i=\xi^i$ for all $i$, which is exactly what you want to see.
Edit (to address the issue on dimensions raised in your comment): This again mainly is an issue of notation. Since you have denoted points in $M$ by $x$ and local coordinates by $x^i$, I have tried to use similar notation for tangent vectors and this gets a bit misleading. What I have actually shown above is that the tangent vector
$$
T_{Y_x}p\left(\sum_i\alpha^i\tfrac{\partial}{\partial x^i}|_{Y_x}+\sum\beta^j\tfrac{\partial}{\partial \xi^j}|_{Y_x}\right)=\sum_i\alpha^i\tfrac{\partial}{\partial x^i}|_x.
$$
So for fixed $Y_x$, there is an $n$-dimensional affine subspace in $T_{Y_x}TM$ that gets mapped to $X_x\in TM$. But the actual pre-image of $X_x$ in $TTM$ is the union of all these affine subspaces for all the points $Y_x$, which form an $n$-dimensional vector space. So it looks like the product of $\mathbb R^n$ with an $n$-dimensional affine subspace of $\mathbb R^{2n}$ and hence has dimension $2n$ as expected. In the expression that you wrote in the question, the $n$-missing dimensions come from the free tangent vector $\xi\in T_xM$.
Even easier, if you extend what you know about local coordinates on $TM$ to $TTM$, you see that in the notation above, we get local coordinates $(x^i,\xi^j,\alpha^k,\beta^\ell)$ on an open subset of $TTM$ and in these coordinates, we get $\pi(x^i,\xi^j,\alpha^k,\beta^\ell)=(x^i,\alpha^k)$. Hence the pre-image of $(x^1,\dots, x^n,X^1,\dots,X^n)$ has $2n$ free parameters (the $\xi^j$ and the $\beta^\ell$).