Roll For Shoes – Does the advancement system work for longer campaigns?

I’m about to start in on a new campaign with the Roll For Shoes system, but I’m concerned that the characters will swiftly outstrip basic and intermediate challenges as they grow in dice.

In the title I mentioned "longer" campaigns. I’m defining "longer" as at least 72 hours of game time spread out over maybe 18 sessions, with hopes of room to grow.

Here is an example:

Ryan has Do Anything 1, and begins a life of roguishness. He starts breaking into houses and achieves Skulduggery 2, starts using lockpicks for Tools of the Trade 3, then eventually gets to Lockpicking 4 and maybe Safecracking 5.

Meanwhile, the GM needs to provide appropriate challenges for Ryan. When Ryan starts out, he somehow has to break into a house with one die. If he can manage that, the GM will later need to provide an appropriate challenge for Ryan’s 4-die Lockpicking skill.

From a story perspective the GM can always provide stronger locks and reasons, but by my very rough estimations getting a character to a four die skill could easily happen in a 4-hour session if the game is moving smoothly.

Does the RFS advancement system work for longer campaigns?