hey tater,
always start with basic and learn the rooting step by step. you can jump around with latest methods out there, but that's not going to get you results when you can't see what's going on and adjust things as needed.
you want to make sure that cuttings have at least 1/4" roots before moving to the cups. that means, you can use shoebox, or ziploc baggie to initiate the process. the whole idea is to monitor what's going on and adjust to the need of the cuttings. once you get used to the whole process, things will just become routine.
put the cuttings in 1 gal freezer ziploc with well squeezed out paper towel wrapped around them, i like viva, and place it in a location that has more or less steady temp of 75-80. in 2-4 weeks, you will see the roots. you can use s. moss if you don't like paper towel, or can do jon's improved baggie with soil mix. air them out once a day or 2 days.
once it has root, carefully move the cuttings to a cup with 50/50 perlite/seedling soil. make sure to pre-wet it, but just like the paper towel, make it just moist enough to provide needed water to the cutting. if it's wet, it will rot the cutting since water has no where to go.
same as before, cup goes into humidity bin like your set up, but at a location where there is some sun light and constant temp of 75-80.
once the roots have reached the cup and you can clearly see the roots, it's time to consider moving them to 1 gal container. more roots you see, better your chance of that cutting turning into a tree.
in every stage, you have to learn how much water is good for the setting, and never more than it's needed, unless you are using some sort of system to drain the excess water. check regularly to prevent mold and to air out the cuttings.
faster you move from stage to stage, better chance of avoiding mold and rot issue. spring rooting is the best idea for the people doing this for first time. once the outside night temp is above 50, 1 gal can be left outside.