I think your main concern about the bags sitting for so long is valid. The material going into the bags needs to have an adequate moisture content to get them to conform and set properly, if the material sits and dries, even if you retamp, it won't necessarily be the correct consistency for a strong brick. The labor on bagging isn't horrible. Instead you could fill
enough bags to do a single layer, then lay and tamp. Use the machine to lift the bags for higher on the walls and save yourself the lifting. If UV is a major concern-get good uv protected bags and after you do two feet, spray with a clay slip to help keep the sun off.
Bags take some unique muscles to get them in place and tamped. If you've never done a building, bagging and tamping sucks for about a week, but then your body begins to figure it out and it you'll be doing double the number you could the first week.