PLINK needs a structured data (PED and MAP file or binary version of those). R can handle more complicated data. PLINK is easy to run, underlying code is C. R can be slow and sometimes needs a more powerful infrastructure. R is defiinitely more versatile, especially for meta-analysis, time to event etc.
I agree with Joseph, I tried plink to analyse some 'plink formatted' data but it failed because there was no .ped file. I went for R because it was more flexible to read arbitrary data sets, and more flexible in follow-on analyses and plotting options. You might prefer plink if you don't like programming, but then again it doesn't look like it would be a 'simple' option.