Kevin
I'm not sure it's as simple as the tyres not suffering lap time disadvantage because of high wear, there are other factors at play here. I've been running some tests in a private league and it appears to me that fuel load and the removal of dirty air are contributing to the behaviour we are observing.
Even before the recent changes, in a 50% league I host it was quite common to see teams running softs down to 25% - 30% to avoid doing an extra pit stop.
IMO the tyres do slow as they wear but this is negated by the fact the fuel load is decreasing towards the end of the stint. Maybe the balance between the lap time penalty resulting from tyre wear and the gain resulting from lower fuel load needs to be tweaked.
I think when the league rules are introduced early next year, for leagues that choose to run a "no refuelling" rule we will see that tyre wear is a handicap. In a no refuelling league, at any point in the race all cars will have similar fuel loads and then we will get to see the difference between a car running softs at 30% and another running new ones. My guess is the new tyres will be faster and the undercut might come into play.
The other factor is the removal of dirty air. I understand why some managers have welcomed this because of the benefits it brings. Gone are the strange first laps where you might gain or lose 10 places and since the changes were implemented reports of overtaking in the pit lane have dried up. However, because cars are able to follow the one ahead more closely it does seem to encourage the formation of long DRS trains and cars on worn tyres can sit in the train and be dragged along doing faster lap times on worn tyres than they would if they were on their own.
I'd like to think something like your comment, but the capacity of the tires runs under 20% especially the soft and not seeing losing of performance or minimal, then what's the point of remove dirty air to encorage overtakings if and the end those tires will long lasting with similar performance, it needs a better balance, as you said would be interesting next year about fueling or not.