Sending good vibes to all of my trans comrades 
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These are all great! Of them I think 5 might be the easiest to coord on account of its versatility as a JSK allowing you to use it as a spring dress on top of a blouse in addition to it being a summer dress. Similarly I think 4 would look incredible depending on how you accessorised it, it's probably my actual favourite among these. But if your goal is primarily to challenge yourself 8 is probably best to figure out how to make the dropped bishop sleeves work.
My current go-to style is pretty punk, so I'm planning on accessorizing a dress like this with like a chunky spiked choker, fishnets, black boots, a bunch of DIY jewelry, maybe a chest harness when I eventually get one. Plus heavy eye makeup and black lipstick. But I really admire lolita and in the past I was actually thinking of trying to get a coord, so some of that bleeds into my designs at times. Currently, I'm pretty set on 4 as the one I try to make first, and 8 probably as the second.
Oh right I didn't mean specifically as a lolita coord, I moreso just meant that 5 would be easy to coordinate into a lot of different outfts. I'm just too lolita brained so I use lolita terms for everything fashion related 😔 Those accessories definitely sound like they'd go well with 4, especially the jewelry and choker, so I definitely think your choice of doing it first is best.