The answer to 1) is no, but it is not easy to find examples. In the paper
Dark, R. S.
A complete group of odd order.
Math. Proc. Cambridge Philos. Soc. 77 (1975), 21–28.
a group $H$ of order $3 \times 19 \times 7^{12}$ is constructed, which has trivial centre and is isomorphic to its own automorphism group. So $H \times C_2$ has even order but with odd order automorphism group.
Note that it $|G|$ is even and $|G/Z(G)|$ is odd, then $G$ is a direct product of a group of odd order and an abelian 2-group $T$, and if $|{\rm Aut}(G)|$ is odd then we must have $|T|=2$. So all examples must be similar this one (although the odd order direct factor would not necessarily have to be complete).
As for 2), that sounds as hard as determining the structure of all finite groups!