1 Were I a Grammar Nazi, I'd say something about this being the subjunctive mood.

2 Yes, there's past subjunctive ("were the strike still on..."), but then you run into this:

Another traditional rule states that you are not supposed to use the subjunctive following verbs such as ask or wonder in if clauses that express indirect questions, even if the content of the question is presumed to be contrary to fact: We wondered if dinner was (not were) included in the room price. Some of the people we met even asked us if California was (not were) an island.

I was taught to apply the rule to any indirect question ("Don't you think"=="Don't you wonder if..."), but I suppose the point could be argued.

The American Heritage usage panel also cites 200-years-worth of "even well-respected writers" using the indicative in place of the subjunctive (was instead of were).

I guess what bothers me in the sentence is the presence of the modifier writers'. To my ear, "...writers' strike were..." clangs in the manner of an agreement problem, which seems ample reason not to use it. Better: "Don't you think he wishes (that) the writers were still on strike."

(Or maybe I just prefer the indicative.)

3 It was a bit awkward, wasn't it?

Most people, I think, would rather hear the indicative, especially if the alternative grates on their ears.  I think I'd have reworded that example before letting it go, perhaps like this:

"The writers' strike ended weeks ago, no doubt much to his dismay."

Then again, anyone editing my stuff is subject to apoplexy.

4 Your variation trumps mine by being stronger rhetorically. Well done!