On page 17 of this pdf, http://www.math.uchicago.edu/~may/CONCISE/ConciseRevised.pdf, the Van Kampen Theorem is proven.
That is it is shown that for any covering of a space $X$ by a family of open path connected subsets $\lbrace U_i\rbrace$ closed under finite intersections, then the fundamental groupoid $\pi(X) =$ colim ${\pi(U_i)}$ Where the the category on $U$ is has the ${\pi(U_i)}$ as objects and inclusions $U_i \subset U_j$ as arrows.
Now the theorem is proven by showing that the required universal property is satisfied, that is that given any groupoid $G$ with family of maps $f_{U_i}:\pi(U_i) \to G$ such that the associated diagram commutes (that is that if $U_i \subset U_j$ we have $f_{U_j}|_{U_i} = f_{U_i}$) we can find a unique family of maps $f^*: \pi(X) \to G$ such that $f^*|_{\pi(U_I)} = f_{U_i}$.
For $a\in U_j$ we can define $f^*(a) = f_{U_j}(a)$. This is obviously unique and is well defined because if $a \in U_j, U_k$ we have $a \in {U_j \cap U_k}$ and $f_{U_j}|_{U_j \cap U_k} = f_{U_k}|_{U_j \cap U_k}$.
For a path $\phi: x \to y$ with $x, y \in X$, $f$ is covered by U and thus has a finite subcovering $\lbrace U_i\rbrace$. Now denote the restriction of our path to some path in $U_i$ $\phi_i$. It seems celar that we can find proper endpoints to do this. We can then define $f([\phi])$ to be the composite of all such $\phi_i$.
I think I can understand why the actual steps in the proof are valid, but the theorem seems to require that the sets involved be path connected despite that at no point the actual proof employs this. Can somebody please try to explain what part of that proof is invalid if the $\lbrace U_i\rbrace$ involved are not path connected? Why doesn't the map constructed still work?
I believe you are right in pointing out that the proof of the grupoid version of the theorem is still valid even after we drop path-connectedness assumptions.
However, in most algebraic textbooks Van Kampen theorem is stated in terms of fundamental groups and in fact this is also what Peter May does on the very next page. Here the path-connectedness is crucial, as one wants the fundamental grupoids of the open sets in the covering to be equivalent to fundamental groups (seen as categories). This is a possible explanation of this unnecessarily strong assumption given already in the grupoid version.