1.

Hobbit alias. Frodo was cautioned to use an alias when he left the Shire. He was to be called Mr. Underhill.

UNDERHILL

2.

#4 has an ability used in this game turn phase.

SKIRMISH

3.

This minion's name was misspelled in its first (Fellowship of the Ring) incarnation and received errata to make it match the later versions. His name is related to the number of Rings of Power forged for the dwarf-lords. What was the misspelled version?
Originally named Úlairë Ostëa (the Bony Nazgul, perhaps?), Nazgul the Seventh ("Seven for the Dwarf-lords in their halls of stone...") is properly known as Úlairë Otsëa.

ULAIRE OSTEA

4.

There are 14 versions of Gollum and Sméagol (not counting any that appear in Shadows). The answer to this clue is one of the 14 subtitles. Given clue #6 and the number of letters in the answer, there are two subtitles that look like they would work – Gollum, Vile Creature, and Sméagol, Poor Creature. But the only way to get letters that will lead to the final correct card title is with Vile Creature.

VILE CREATURE

5.

A keyword possessed by #6.

DAMAGE

6.

This minion's race happens to be the same as the second word in the answer to #4.

WATCHER IN THE WATER

7.

Card title with collector's number X Y Z, where:

• X = the site number on the original version of one of the "new" Shadows sites revealed so far = 4
• Y = the first letter of the last word of #8 = R
• Z = the number of versions of The One Ring in the game (all printings of The Ruling Ring count as just one version) = 6

At the time of the contest, Cavern Entrance (old site 7), Moria Stairway (old site 4) and Anduin Banks (old site 8) had been revealed. Sets 7 and 8 have common cards in slot 6, and they don't have the correct number of letters indicated by the blanks for this clue. So it must be 4. Collector number 4 R 6 is Constantly Threatening.

The six versions of The One Ring:

• The Ruling Ring (1 C 2, 4 C 2, 7 C 1)
• Isildur's Bane (1 R 1)
• Answer to All Riddles (4 R 1)
• Such a Weight to Carry (7 R 2)
• The Binding Ring (9 R+ 1)
• The Ring of Rings (11 R 1)

CONSTANTLY THREATENING

8.

The last word of #6 is related to a feature of this version of The One Ring. What is this version's subtitle? Often known as the "Water Ring" (as opposed to the "Grass Ring", the "Fire Rings", the "Snow Ring", etc.).

ANSWER TO ALL RIDDLES

Highlighted letters: EHMHTERMETREOEIRR

Clue: Additional drink makes Mr. Brandybuck comparative (but not superlative).

Card title: THE MORE, THE MERRIER
"Merrier" is the comparative form of "Merry", while "Merriest" would be the superlative.

Additional question:
Did the subtitle in #4 belong to Gollum or Sméagol? Gollum