Rolling a grass strip with a heavy roller is a disaster, you compact the upper layer of soil and wreck the natural drainage.
Depends on location and subsoil:
Our strip is on the site of a WW2 USAAF airfield carefully chosen on the highest ground for miles around with a well draining sandy/gravel subsoil.
The rolling smooths it out a treat, helps repair the divots taken out by the chavs in their Astras and makes absolutely no difference to the drainage.
Strip is flyable all the year round even after the heaviest of downpours.
Except right now when its under 8 inches of snow.....
Cusco.