Hi ATB,
I tried to squeeze a lot into this response, so it may feel that I am 'rambling' at times.
Sorry the lessons have been expensive, but at least you recognize that adjustments are often necessary. Obviously we love it when iron condors go quietly into the night, but that does not happen often enough to make this a mindless strategy.
Expect to take losses. It's impossible for iron condor traders to make money every month. I once had a 14-month streak, but I know that will never happen again.
In replying to your questions, please understand that I am telling you how I think about making adjustment decisions. That means I'm sharing what suits my comfort zone.
Also understand that there are so many different personalities that not everyone can agree on what works. Clearly I believe my suggestions are good methods to follow, but I do not recommend them as gospel. What I do recommend is that you consider my ideas and then decide if those methods are suitable for you. If not, they may give you ideas that allow you to find alternatives that suit your personality, trading style, comfort zone etc.
1) I do NOT try to extend break-even points. In fact, I strongly believe you will be far better off if you ignore break-even points. Once I own a position, I no longer worry about whether it's making or losing money. I manage risk, not profits. I do what I believe is necessary to make the most money - or lose the least money - from the current time. It does not matter how much I have gained or lost up to this point. My position is what it is, and I must decide whether to add to it, hold it longer, or adjust (and that includes exiting). What matters (to me) is how much I have to gain or lose going forward. If risk is too high, I modify the position. If potential gain is too small (because the remaining premium is small), I exit the position (to lock in the profit. But, I don't think of it as taking profits; I think of it as 'there's too little reward for holding longer'). That works for me. If I do a good job managing risk, the profits will be there (in my account).
2) I don't specifically manage risk by delta, but being aware of the total delta of your position is important. I consider 'what happens' if the index moves another 1 or 2%. How bad can this get? I look at the risk graphs and think how far must the index move before I lose $X (X = 'too much'). If I think there's a high probability of losing 'X' then it's time to do something.
I'll say this about delta: If you establish a maximum position delta, that will work as a boundary for your comfort zone. Just remember that if you eventually trade more contracts, that delta number will have to be increased.
But, my primary indicator is that I hate when my short option moves into the money. At that point I must do something - even if I have already made previous adjustments. One other iron condor strategist whom I respect, suggests that having your short options move to within 3-5% of being in the money requires a full adjustment (exit or roll).
I also note that Erin adjusts when the delta of the short option reaches 20. He adjusts very aggressively. I've communicated with people who firmly believe that no adjustment should ever be made to an iron condor. To me, those are extreme ideas and you will probably be more comfortable somewhere in the middle.
3) Gamma is the most important of those greeks. Gamma tells you the rate at which delta is changing. If delta is becoming too large for your comfort zone, you must be aware of how fast that delta is moving against you - and that's gamma. The higher the gamma, the more quickly you will want to make an adjustment.
When I own extra gamma, as I do when I buy extra options as insurance, I have staying power because that gamma soon turns the deltas in the right direction. But staying power is not 'stubborn power.'
I don't manage each iron condor position as a standalone position. I manage the risk of my entire portfolio simultaneously. If I have a bunch of iron condors (I do), of course I adjust the riskiest one first. But, if I own enough extra puts (I do right now), I am a bit less concerned with the downside. I still adjust as needed, but there is less of an emergency. When I no longer need my extra long options, I sell them.
I am aware of the other greeks, but don't dwell on them. Iron condors traders are short vega. If you feel you have too much negative vega (the volatility component in the value of an option), there are ways to pick up vega: buy a few extra options or perhaps open double diagonal spreads, instead of iron condors.
4) Opinion about adjusting methods covers a very wide range. I don't believe anyone is exactly right because we all have our own needs - financial and psychological to satisfy. In other words, if you would personally find it devastating to make an adjustment, only to see the market reverse - and the result is that a position that would have been a winner has been closed at a loss, then adjusting is probably not a good idea for you. You want to avoid those feelings. If you can keep your emotions in check, that's wonderful (essential). But, if you cannot, at least try to avoid putting yourself into a position in which you may be emotionally clobbered.
I don't believe in 'playing results.' I believe you make the best decision you can at the time a decision must be made, and that's the path to success. In fact, I don't check back to see how I much I would have made had I done something different. I keep emotions out of the trading game.
Here's my bottom line suggestions for you.
a) Assume you define your comfort zone boundary as: when the short option gets within 1% of being in the money - although you can choose any point.
Before that happens (choose your own preliminary adjusting point), adjust 10 or 20% of your position. You can do that by closing some of your position. You can buy in 10-20% of the deltas as protection. If you are short a 500/510 put spread, I'd suggest buying 520 puts, rather than further OTM puts. Yes, these are costly. [Cheaper insurance can be had by owning pre-insurance.] There are other choices, but the point is: do something small.
If the underlying moves even nearer to the boundaries of your comfort zone, do more, leaving only 50-60% of your original position unhedged.
At some point, exit the whole position. If you do that, it's usually best to also unload the extra options you bought as a partial hedge.
Please understand, if you don't like the prospects of your position, then get out. Don't exit piecemeal and don't hedge in stages. If you don't like the position there is no point in holding longer.
I cannot tell you exactly what to do, because I just don't know the right answer for you.
5) Rolling. At any time you want to make an adjustment, rolling all or part of the original position into a newer one is an acceptable thing to do. One requirement: Do not roll just to do something; you must like the new position and want to own it. If there is no suitable roll, then just take your loss and wait for a better time to make a new trade.
I hope this helps. Your own experience is going to help guide you, but I know you need some ideas to get started. You may want to reconsider how you choose iron condors - if you find you are adjusting 'all the time.'