My 2 cents on that big thick cutting on the left:
If you are able to keep it in a humid environment (rh 85% or so), I do not think it will be too bad to have the top sticking out of the bag. It should not dessicate in that environment.
If you plan on keeping it indoors in a heated area over the winter without somehow adding moisture, the 35% humidity in climate controlled winter air may dry out any exposed part of the cutting over the course of a few days or weeks.
Two possible suggestions:
1. Use a larger container than the 8 inch bags. I have used clear plastic 2 liter bottles, apple juice containers, etc. These should allow you to monitor root development a bit and should be tall enough to contain the cutting better. You will of course have to cut the top off of the 2 liter bottle. I actually cut the top and the bottom off, then tape the bottom back on, thinking that when I am ready to transplant I can just remove tape and stick it in a hole more easily.
2. I have been using the new baggie method on a bunch of cuttings I started in November. I have been keeping them inside but for humidity have them in a large rubbermaid container with water inside for moisture. I used hardware cloth and 1 inch wood to make the floor to keep them elevated off the water on the bottom. I open it up once a day. Humidity stays above 85% inside so there is no problem with drying out. I watered initially but really have not had to water at all since (over two months ago with very dry indoor air). Very little moisture escapes the container so there is little need to add any. If you wanted to keep the container open more often you would have to add some water from time to time. I have not had any problems with mold