I don't think you need to double box. I've ordered from them before, single box does the job just fine. Chukkas aren't fragile bro. Unless of course you like your shoe boxes in perfect condition, then by all means go ahead haha.
I would say $243 is a reasonable price for a pretty scarce shoe. Let's say you ordered the shoes when they first released. $170 plus tax comes out to about $185. That approximately $58 mark up you would spend if you were to buy them right now, you won't even feel it once you get the shoes. They look great in pretty much any outfit, low maintenance and super easy to clean, and one of the most comfortable and stylish shoes out there (IMO).
Have you considered other colorways? The Wolf Grey/Electric Green Chukkas can be obtained for significantly below retail. I ordered a pair for my uncle from Concepts for $100 shipped.
Or if you really want to just enjoy the joys of Flyknits with a Lunar sole, Flyknit Lunar 1s in the black/white colorway are on sale on NDC for $90 (about $100 shipped). Almost the same shoe, given differences in the midsole, outsole, and cut.