Yeah, a 24' ladder will let you access that taller section of roof safely, even if you have to approach it from the side or rear elevation. there is almost always a slope that can be accessed from a 2 story ladder.

I got the Werner with the adjustable legs and really like the stability regardless of terrain.  Check out that link, I got a 24' and a 16' with the adjustable legs. 

Also check out this link for the "Walk Through" which will add 3' to the length of any extension ladder.  I really, really like this thing and use it on my little 16' ladder every time I go on a roof, so I don't have to step around the side of the ladder to get on the roof.  It adds some weight to the end of the ladder - but still not nearly as heavy as a fiberglass ladder.

I wanted a 2 story ladder, and was debating a 28' or 32' for those times when the house is on a raised foundation and a 24' might not be enough.  The extra 3' on the walk though addresses that issue, and you can leave it off if you don't need the length.  But when I am 2 stories off the ground - I like to walk through the center of the ladder.  With cougar paws, and if it is bad-ass I use rope and harness.

These are on the ladder rack with a little Giant inside the van for getting in those tight closet attic access doors.  Pull off one of the sections so the narrow part can poke into the attic - some of those older houses are a challenge to get into the attic and find the leak.

Speaking of double pulls... This season where I was working, many of the houses are on the hillside which have mostly 2 1/2 to 3 story roofs.  Many of the Insureds had contractors that were from out of town, almost none of whom had even a 24' ladder.  I carry my 28' Werner ladder.  When I asked them how they inspected the roof or even measured it, the most common response was we did a double pull or we looked at the porch roof.  My question is this.  How many of you would let a contractor climb your ladder?

I would, and I do. Mind you I tie off to the fascia, and don't set my ladder up one a stack of milk crates...

I may not invite the homeowner or contractor up my ladder - but if they ask I'm not going to deny them, as long as I know it's set up well.

I also use one of these Ladder-Max things http://www.buyladder-max.com/  which makes the ladder incredibly stable, doesn't tend to want to slip sideways. In those photos, they show the ladder kind of far away from the gutter.  I set mine up so it is very close to the gutter but not touching.

I think you would almost have to have the equalizer legs I mentioned earlier (adjustable legs) because when those "stands" sit on the roof, they affect the angle of the ladder. You can't just lean the ladder against the eve and let it find it's place - those "stand off" things are going to put it where they need to go.  Pull the ladder out one more rung, and it may be too far. But with the adjustable legs, you can fine-tune it so the angle is right on.

Takes longer to get set up, but this thing will not crush gutters and when you combine it with the "walk through" thing - I feel pretty comfortable letting people on my ladder. I'm sure all of us have better than average equipment, so really it comes down to the LIABILITY thing. But I let people up on ladder if they ask nice.  I would not agree to loan out my ladder - I like to know that my stuff hasn't been dropped, or slammed around when I'm not looking.
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Back to the original thread - I won't knowingly climb a roof in the rain.  Sometimes you get caught with a sudden rain - if it's a steep roof I head for the ladder with the first drop.

Climbing a roof period is dangerous business and falling off happens to even the safest of roofers, adjusters, etc.  Sounds like a good warning and I will take heed of staying off those wet roofs.

My opine is I have never lost business from any source; because I did not have a 2 story ladder or would not climb some roofs. My statement covers about 20,000 closed roof claims, however I may be passed over on some losses, who knows ?

Tim, if you and Larry like to play cards, maybe I'll travel south to OKC and we can have a session.  Need a fourth though, and I don't know if Larry has any friends.  He doesn't say much.