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The basic ida is to first do a study on the purely pQCD level. Different shower algorithms should be compared at LO+PS level first, along with their recommended variations.
Having cross-validated these uncertainties between different algorithms, matching/merging approaches should be included and an assessment on accuracy improvements should be made, again cross-validating different algorithms.
A comparison to analytic resummation (where possible) and at different levels of perturbative accuracy is desirable. The range of observables should be kept small and concise, ranging from quantities which exhibit resummation, transition and fixed order regions, but also including these observables, where shower uncertainties are expected to indicate large hadronization corrections, as well.
A preliminary list includes: