Probably will since Samsung released 4.4 for Galaxy S4. But one thing for sure you won't get the new 5.0 look because of touchwiz.
No, from what the videos show, your defiantly getting a bit of the Lollipop work, actually a lot more than ICS/JB/KitKat look. Google has pressured them to be a bit closer and they are.
Day L releases = Files ready to flash for Nexus
OTA = Either Moto X or Nexus 6
Nexus is done, Motorola is finishing up.
HTC.
Samsung is getting started. (early 2015)
LG updates their devices.
Samsung ends around Mid-slightly late 2015.