In my humble opinion, applying S's syntactic sugar on top of Scheme-forged core did more bad than good to R. Most of R's quirks stem from the authors' desire to keep it as compatible with S as possible.
As for the two approaches to solving problems (TIMTOWTDI vs Python's "one true way") I think that's a matter of personal preference; I, personally, appreciate the freedom that R gives me. Also, it might be anectodal, but I believe that - to some extent - it promotes thinking "outside the box", especially when you work in a team and review others' code on a daily basis.
On the other hand, if it was not for that compatibility with S we would not be having this conversation: R would be just a footnote in the history of statistical computing like Lisp-Stat.
Perhaps having a fixed (and commonly agreed on) set of design patterns - like in Java - makes development easier and smoother, but most of the projects I've worked on have proven successful, so maybe it's not that bad either... :-)
Was S "really, really old" when it was re-implemented in R? Gentleman and Ihaka first announced R in 1993 (26 years ago!).
The development of S started in 1976 (i.e. 17 years before R was first released). R was a implementation of S3, "the New S language", which was a major rewrite done in 1988 (it was just five years old when R was announced!).
R is wonderful (and has multiple dispatch, thank you very much), but it's definitely not as familiar to developer types as Python is. R has lots of weird quirks (a[1] vs a[[1]] vs a[1,]) and uses function based generic programming rather than object based generic programming.
Because of the re-implementation of S, it has lots of odd quirks and multiple ways to do things, which Python tends to avoid. Python is definitely more consistent from a programming point of view, but R is a more cohesive system from an analytics point of view.
But yeah, lots of people are hateRs (unfortunately).