The chiles in the first photograph are not roasted far enough. Generally, you want the chile skin charred black and blistered. Even the second photo with the partially charred chiles really haven't been roasted long enough. Those chiles will be difficult to peel in the uncharred areas unless they've been allowed to steam.
We just did 80 pounds of chile this past Friday, and all of the chile was roasted far more than what is shown in the second photo. We get our chile directly from a farm. They use propane, wire-basket, rotary drum roasters with direct flames on the chile. They generally roast the chile for about 15 minutes and then dump it into large plastic bags where it steams as you drive home.
The chiles are thoroughly charred and blistered, and by the time you start removing the skins, it will almost fall off of the chile just from handling it.
If you take the hot, charred chile and put them between damp towels and steam them, or put them in plastic bags and steam them until they're just slightly warm, the skin should come off easily.
There are two reasons for taking the skin off of the chile. In some uses, the skin turns bitter as it cooks. Secondly, the skin is tough and if you leave it on the pepper, as the chile cooks it will separate from the meat of the chile and you'll have these tough, unpalatable skins in the food.