Answer: 544

Solution:

The assignment works if and only if no town has all four roads inbound or all four outbound. One direction is clear: an all-inbound town cannot be left, and an all-outbound town cannot be reached. Conversely, suppose every town has an inbound and an outbound road, yet town $B$ cannot be reached from town $A.$ Let $S$ be the set of towns reachable from $A$ (including $A$) and $T$ the set of towns from which $B$ is reachable (including $B$). These sets are disjoint, every outbound road of a town in $S$ stays inside $S,$ and every inbound road of a town in $T$ comes from inside $T.$ Since $A$ has an outbound road, $|S| \ge 2,$ and similarly $|T| \ge 2;$ as $|S| + |T| \le 5,$ one of the two sets has exactly two towns. If $S = \{A, X\},$ the outbound roads of $A$ and of $X$ must both stay inside $S,$ forcing the single road between them to point both ways — a contradiction (and $|T| = 2$ is symmetric).

Now count assignments with a bad town among the $2^{10} = 1024$ total. Choosing a town to be all-outbound ($5$ ways) and orienting the remaining $\binom{4}{2} = 6$ roads freely gives $5 \cdot 2^6 = 320$ assignments, and there can be at most one all-outbound town. Similarly $320$ assignments have an all-inbound town. Assignments with both are counted twice: choose the all-outbound town ($5$), the all-inbound town ($4$), and the other $3$ roads freely, $5 \cdot 4 \cdot 2^3 = 160.$ So $320 + 320 - 160 = 480$ assignments fail.

The number that work is $1024 - 480 = 544.$