Harass Enemy says that your opponent is treated as Weary. However it says nothing about multiple opponents. I ruled that it can only affect one opponent and you choose which one before any of them attack.

Our Woodsman player, of course would like it to be the other way round, but it a/ doesn't feel right to me that a single dog can harass 3+ enemies at once, and b/ it seems like it would be too strong as an ability.

Thoughts?

I'd agree with your assessment. The dog is barking and biting continuously at the opponent in order for the Wearied state to continually apply. It can therefore only do it to one opponent.

I agree as well. It is plenty strong enough dealing with only one target at a time (particularly when rolling Protection tests).

I have also considered a maximum attribute rating for the targeted adversary. It certainly doesn't seem to make sense that a barking, snapping dog would be able to distract Smaug (for example) to such an extent that he would be significantly penalized.

Totally agree with this as well. What do you consider that att rating to be? What about "Hero's valour +3)"?

Suggesting that the dog takes on the courageousness of it's master.

How about the Axe of Azanulzibar as a guide?

Does 6 make sense as a good cut-off?

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Hrm. Yeah, I suppose. I like abilities that scale, I suppose. Maybe that's just a leftover relic from my 3.5 days. I guess 6 is high enough to keep it useful throughout the life of the character.

I think you are missing the point with Harass Enemy. Your interpretation makes it very hard for a player to know where they are with a close combat situation.

A player positioning himself on the close combat mat fully expecting his advantage to count will be justifiably aggrieved that it does not at the whim of a GM.

It is an abstracted skill, like many others in this game, that represents distraction, mobility, or team work between the woodsman and the hound when attacking. I would consider the hound as a large creature and would still represent a presence of sorts.

I think the Smaug example just shows that the correct interpretation is that your woodsman can be mobile around Smaug, but if Smaug burns hate points, or some other ability, this will negate the advantage and the resulting damage is likely to hurt. If Body/Favoured Body are added to hits the results are really going to hurt as you can only ride your luck so far.

Also I would expect Smaug to have other attacks that would get around this sort of ability causing Valor tests and the like. This being the case the fight would nearly always finish one way.

I have player things like D&D where a Hobbit with a dagger can give "flanking" standing next to a dragon even though he/she represents very little threat. This is an accepted manoever that is taken for granted. At the end of the day the Hobbit WILL, most likely, get fried by the dragon and we can all call that "lesson learned".

You are over thinking this and are just making thing more difficult, and literal, than is necessary.

It is the case that the rules are clear and this sort of tinkering can be counter productive and hard to play all round.