Clearly, the respective merits depend on the data under analysis, and although they depend in non-trivial ways on what actually causes data to be distributed as it is, we can at least consider two extreme cases.
Data is virtually error-free, it just has legitimate outliers, but you don't want your results to be severely affected by them. For instance: in a distribution of wealth, there are horribly rich and horribly indebted people that would bear an excessive weight in your estimates. Now, you don't necessarily want to ignore these people, you just want to ignore they are so rich, or indebted. By winsorizing, you treat them as "reasonably rich" or "reasonably indebted". (Notice that in this specific example if you were only looking at positive wealth, taking a logarithm might be preferable)
The underlying distribution is nice, possibly normal, but there are (few but relevant) errors in the data and you know it is only such errors that cause the outliers. For instance: in a distribution of reported salaries, a few survey participants might have mistyped, or reported in the wrong currency, their own salary, resulting in unreasonable amounts. By trimming, you exclude outliers because they really don't provide useful information, they are just noise (notice you will have some noise left in the distribution, but at least you remove the noise that would disproportionately distort your analysis).
Then, outliers in real data are often a mixture of data error and legitimate extreme values, which it is not obvious to interpret.
The recommendation to always parallel your winsorized/trimmed results with the full results is always valid, but for two slightly different reasons. In the first case, to warn the reader that you do not claim you are talking about the actual distribution: rather, you study a modified distribution which de-emphasizes extreme values. In the second case, because you claim you are talking about the actual distribution, but you must warn the reader you more or less arbitrarily decided what in the data was actually noise, not information.
On a more subjective note, trimmed results (and the difference with full results) are often easier to describe correctly, and to grasp intuitively, than winsorized results.