I think maybe you are complicating things a bit. Here is some advice.
Make your past work experience overlap as much as possible. If you were "unemployed" for 1 - 2 months in the past, just make the dates you switched jobs conjoin. Why? Because it is a waste of time to say "I was looking for a job for 2 months." That type of questioning is for undergrads who generally take the summer off to travel, have fun, research, etc. Non-trads generally are busting their humps trying to get a job to meet their financial obligations.
If you have multiple volunteering experiences that are similar in nature, put them all in one slot, list them and annotate the number of hours for each one.
Write down all your secondary questions and the answers you have written to them. Re-use for other secondary applications. After a while the questions repeat, and trying to remember what you wrote down several days ago can be annoying. Being a non-trad I doubt you have 3 hours per day to spend on each secondary as well.
Ultimately the most important slots that you should focus on are your 3 most significant experiences.