It seems as though the thumbtack in geometrical vectors is equivalent to the wedge product of two vectors $A \times B=C:$
$$A^\mu e_\mu \wedge B^\nu e_\nu=C^{\mu\nu}e_\mu\wedge_\nu$$
which would return an oriented parallelogram in $\mathbb R^3:$
Weinreich then considers the “cross product”, which leads him to further kinds of vectors. The cross product of two arrow vectors turns out to be a “thumbtack”, a kind of oriented area.
Probably the pin part in the tack makes reference to the right-hand rule, while the round head is a surface. However, its circular shape is as unsuggestive of a parallelogram as it gets. Very respectfully, I would presume something like a patio umbrella to be more fitting, but, again, the question is not "would it be better to ..." but rather, "is there a reason for":
My question is whether the circular shape of the head of the tack is intended to make reference to a mathematical point, or it is not the best aspect of an otherwise helpful analogy.

Stacks and tacks is very catchy, and the thumbtack analogy definitely conveys the idea of an oriented surface seen from a topological standpoint.
Quoting the free online available pertinent passages of Gabriel Weinreich's Geometrical Vectors:
So the shape of a tack is immaterial, and a pair of vectors define a tack corresponding to the parallelogram they subtend.
A thumbtack is a $2$-vector, eating up two $1$-forms. If, instead, only one $1$-form is provided (a stack), the result will be an arrow - i.e. a $1$-vector:
$$\begin{align} &\underset{-}B \times \underset{\circ}T\\ &=T^{\alpha\beta}\, \mathrm e_\alpha \wedge \mathrm e_\beta\; \left( B^\mu\mathrm e_\mu,\cdot\right)=C^\beta\,\mathrm e_\beta \end{align}$$
This can be visualized as a deforming thumbtack keeping its area constant, and defining an oriented segment (vector) as it reaches across one of the gaps in the stack: