Here are some additional points FWIW.
In filter design the peak sidelobe level (PSL) is an important stopband parameter because it is going to decide the worst-case attenuation. For example, the PSL of Hann-window based LPF is $-43.9$ dB, whereas for the Hamming-window based LPF it is $-54.5$ dB. Hence, the latter is preferred for filter design. Note that the roll-off for these are quite different: $-6$ dB/oct for Hamming and $-18$ dB/oct for Hann. Hence, the latter is far better suited for spectral estimation (because its faster roll-off will allow nearby weaker sinusoids to show up in the spectrum, unlike the Hamming window). The faster roll-off is inconsequential in filter design because it is the PSL that decides the worst-case attenuation.
For a given window length N,the energy should be normalized for fair comparison between different designs. Hence, if we try to reduce the energy in one region, it has to pop up elsewhere. With this in mind, since the PSL is the crucial parameter as far as stopband performance is concerned, it is intuitively clear that if we make all the sidelobes to be of the same height. we can forego roll-off. Roll-of is a double whammy: not only is it unhelpful in filter design, but also reduces the energy in those regions, which energy has to pop up elsewhere. The transition region is the one that takes the hit in absorbing this energy from the stopband. This also explains why window-based LPFs that are designed using ones having less abrupt transitions have better PSL's but at the cost of wider transition.
OTOH if we make all the sidelobes equiripple, the increased energy in them can be drawn away from the transition region. Thus, equiripple filters have the narrowest transition region among all filters having the same length and specifications. It is a natural consequence of using the minimax error as the criterion. Hence, if an equiripple design is available, that would be the best among all other design choices such as window-based, least-squares, etc.
Note that the Chebyshev window, which is equiripple, is optimal as far as windwos go, but an LPF desinged using this window is not optimal. This is because it loses its equiripple nature after convolution (in the frequency domain) with the ideal LPF's frequency response.