[Update]
Sony and game developers have clarified who will be footing the patch bill, and it's not gamers.
[Original]
The PlayStation Meeting send PlayStation fans into either fits of hype or discontent over the PlayStation 4 Pro. The new system was revealed to feature an upgraded GPU (more than doubled), 4K display, boosted clock rate, and a 1TB HDD. However, it won't feature a Blu-ray 4K player, because most of the user base uses streaming apps.
In order to take advantage of the PS4 Pro's power and the ability to change your gameplay experience (depending on your TV), game developers will need to supply games with an enhancement patch.
If a game was developed prior and released prior to October 2016, it will require a PS4 Pro enhancement patch and games that release after October will not. Unfortunately, it looks like the patches for pre-October released games might cost you.
According to an interview translated by Kotaku, some of the patches will be free while others are not. The Director of SIE Masayasu Ito sat down with Game Impress Watch who asked the vital question:
Game Impress Watch: For the 4K HDR patch for existing titles, will it cost money? Or will it be free?
Ito: It will be different for each title. I believe it will depend on the thinking of each licensee.
Fortunately, Ito went on to say that first part titles from Sony would support both 4K and HDR.
While I understand why the patch would require a fee, it does require development and labor, I can't even begin to guess at how much the patch would cost.