Wetting the column creates a far more even and secure packing than any amount of physical effort you could attempt to impose upon a bunch of loose dry powder. I agree with you fundamentally that you need a tight pack for a good run, and I believe that rinsing your media is the best way to achieve it. Failure to rinse the media inside the column is also a pretty good way to end up with submicron contaminants in your oil. Furthermore, if there are other issues causing clogging (like a dirty sintered disc, unbaked/clumpy media, over packing, poor vacuum etc) you will know the column is bad and needs to be repacked before you ever put your valuable oil inside.
Rinsing media to observe proper flow and establish a sufficient solvent reservoir is 70 year old chromatography protocol that should not be ignored.
If the OP is having issues with every run and ISNT prewetting and IS packing tight I would bet rinsing the column will solve his issues with the first try.