There were a lot of Plain Finish/Standard Grade Winchester Model 12s & 97s, Remington Model 11, 10 & 17 A "Standard" Grades, etc. giving good service for decades without any checkering.
And a bazillian of the pressed checkerd jobs that sort of feel like flat top checkering does. Not every old gun has had the checkering recut when worn either, so just perhaps the actual function of checkering is a tad overstated.
I like checkering. I like the way it looks, and some, even most, guns would indeed look unfinished without.
One of the best stocks I've ever had the chance to use belongs to a friend of mine who fitted it to a Beretta auto. I believe it's from Wenig. He allowed me to try it before he checkered it. It has a big meaty grip area and handles very well. The owner thinks it's just fine as is and has yet to checker it.
As far as the wuss factor goes, I may be one but I don't wear gloves. I can't even shoot with gloves in cold weather. Some guys do wear gloves, even in the summer. I don't understand how that can help except to buffer the abrasive effect of the sharp checkering.