I took the family to Park City for our Spring Break. I am Plat, rest of family mere OnePass Members - Non-Elites. For the first time in many years I took my own skis. I purchased a soft-side bag, put in the pair of skis and poles and then proceeded to stuff it with gloves, ski jackets, ski pants and other items to cushion it.
We did the self check-in at IAH. I failed to select the "over-sized" option, received 3 luggage tags and the CO rep took them with no issues. We had a 4th bag that I had to designate to one of my other family members and paid the $25 for it.
Coming back from SLC my family took all 4 bags into the airport, checked them through with the help of a Skycap (I was returning the rental) and not only were we not asked about additional items in the ski bag, there was no incremental charge for the over-sized bag OR the 4th piece of luggage.
It seems the policy, as with so many others, is enforced irregularly.