What happens if I use Skiploom's "Floral Path to the Sky" Ability but fail to find a Jumpluff in my deck?
Skiploom stays in play, and since you searched your deck the ability is used up for the turn.
Source: Lost Thunder FAQ (2018-10-20), TPCi Rules Team (2018-11-01)
What happens to any damage counters on Skiploom when it uses its "Floral Path to the Sky" Ability? Do they go on the Jumpluff that takes Skiploom's place?
Any damage counters on Skiploom are removed when it goes to the Lost Zone; they do not transfer to the Jumpluff that takes its place. Special conditions are not transferred to the new Jumpluff either.
Source: Lost Thunder FAQ (2018-10-20), TPCi Rules Team (2018-11-01)