The answer to both questions is positive if $D$ is finite-dimensional over its center $K$, and negative, in general, otherwise.

Q1. Suppose $V$ is a $D$-bimodule over $K$ (i.e., a $D\otimes_K D^{op}$-module), while $W$ is a left $D$-module of dimension $n$, as in your question. Then $W$ is isomorphic to a direct sum of $n$ copies of $D$, hence $V\otimes_D W$ as a left $D$-module is isomorphic to a direct sum of $n$ copies of $V$. So the $\dim_D (V\otimes_D W) = n\dim_D V$, where $\dim_D$ denotes the dimension of left $D$-modules. Now, to answer your original question, it remains to notice that the dimensions of $V$ as a left and a right $D$-module coincide, since both are equal to $\dim_KV/\dim_KD$.

It does not matter in this argument that $K$ is the whole center of $D$, only that $K$ is a field contained in the center of $D$ and $D$ is finite-dimensional over $K$. On the other hand, if $D$ is infinite-dimensional over $K$, it may happen that $D$ can be $K$-linearly embedded into itself as a proper subring. This would allow to define a $D$-bimodule structure on $V=D$ where $V$ is one-dimensional as a right module over $D$ and more than one-dimensional (possibly infinite-dimensional) as a left module over $D$. This would break your dimension formula.

Q2. Left $D$-module maps $D\to D^\ast$ are in one-to-one correspondence with elements of $D^\ast$, i.e., $K$-linear functions $D\to K$. A linear function $l\colon D\to K$ defines a $D$-bimodule map $D\to D^\ast$ if and only if one has $l(xy)=l(yx)$ for all elements $x$, $y\in D$. Taking $l$ to be the trace map (defined e.g. by tensoring $D$ with the separable closure of $K$ over $K$, identifying the result with matrices over the separable closure, and taking the traces of matrices), one can obtain a $D$-bimodule isomorphism between $D$ and $D^\ast$ when $D$ is finite-dimensional over its center $K$.

The above argument can be easily extended to the case when $K$ is just a subfield of the center of $D$ and $D$ is finite-dimensional over $K$ (one just composes the trace map with an arbitrary nonzero linear function from the center of $D$ to $K$). On the other hand, when $D$ is infinite-dimensional over $K$, it is no longer true that $D^\ast$ is a one-dimensional left $D$-module.