Something I've been having a little trouble finding an answer for is the problem of opening with a wing. There are naturally several different methods to tackling this problem, the first and most obvious answer is to both go in together with a "debate" style opener.
The second option is for one person to make a standard approach, and to have their wing occupy themselves somehow for a few minutes while the set hooks so they can join in.

This is where I run into a problem; what should you get your wing to do while you hook the set? He can’t just stand around, as that'd lover his value to the group before he even got a word in, It's not really practical to have him open a set nearby (though that can work on occasion) due to set availability and time constraints, it's hard to act distracted nearby, without making it look set up when you call them over, and because you walk together, you can hardly split up then fake a meet up a few minutes later if you are spontaneously approaching on the street.

What do you guys suggest; I don’t have any bright ideas. Is the first option to approaching with a wing the best? If so, can anyone give me a good example of the sort of opener structure to use?

I have a simple arrangement with my friend whom I go out with the most. Either I approach and he comes in almost straight after me (no problem in killing 1min of alonetime) or he goes make a round in the club, check out who's there. Then he'll join me in maybe 5 minutes or if he finds a target of his own, I'll be gaming without a wing Needless to say, it works both ways.

I think there are two key reasons why PUAs goof up with their Wingman.

a) One PUA is leading the frame too much. His friend is looking at him and the target nervously. This comes across in two ways. The PUAs friend sucks and he is not happy to see him (which lowers the value of the PUA to a degree where he might as well be out solo). The girl senses the PUA's friend DLV and she'll start toying with the PUA. After all if his friend sucks then by nature the PUA must suck if he makes bad associations.

b) Lack of congruence between the two guys. (Please note- I go out solo and use Pivots* and Meta Game* to gain Social Proof). *search forum for definitions.
Guys do a 2 for 2 set. One distracts the "fatty" effectively "taking lead", whilst the other isolates the target- perfect yes?.........
No in the case where girls feel they are being "ganged up" they will throw off verbal curve balls (shit tests) to confuse the attackers. If one guy takes the bait without realising the shit test, the whole system falls apart -women see you aren't "really" friends as you are not working together and being on the same page.

My one and only wingman would fuck up time and time again. Id correct him politely at first, break it down, s-p-e-l-l i-t o-u-t and then say "whatever no chicks tonight!"

I go out solo and have taken on an all girl set of 8s, all tens and closed time and time again.............

If this guy your out with really IS your Wingman- try the following three exercises before heading out to increase congruence.

1) The insult game- like a verbal (abusive) game of tennis mock one another.....no seriously! Come up with inventive ways to mock one anothers dress sense, physical appearance and born physical imperfections. If you friend looks like a Monkey-say "Hey Donkey kong! Did the doctor slap your mother when you were born?"
Then in the next round that person must come up with an inventive reaction. For exampe if I said "Nice trousers- Im going to buy you a belt so they dont fall down" reply "Oh these?- they make it easier to drop them
in a gay bar. By the way if I werent gay you'd so be mine!"
STICKING POINT- If you can insult your friend in this type of environment without him taking offense you have an understanding friend- if not he maybe a serial killer! It will help if girls verbalise your imperfections later. You can also take the wind out of there sales by saying "We had a better example earlier...."

2) Role Playing- very much like that classic show "Who's line is it anyway" (I know you have a US version!) do some improvised acting beforehand. Your Wingman can play the part of "The Chick" and step into the "Wingman" role as well. Silly? No I mean people in all games be it Golf- Ski-ing, Football or Baseball do practice shots before the game.
Think of a scenario to play out just like in the show. The more funnier the better the reaction in the club later!

3) Practice during the day. Take your friend to the Mall- get an opinion opener. "Hey my friend wants to buy this shirt which I think looks gay- can I get a second opinion on it?"