@skategeek that's so cool! I was gonna ask about the break-in period because I heard it was supposed to be really long and really painful for Jackson skates but I don't seem to feel it either whenever I'm trying the boots on. But I've only done it at home so far since I haven't skated for more than a week now since the start of the holiday break. 
I hope the convenience also applies in the rink once I get back! I can't wait to try them on actual ice! 
You’ll often read warnings about overbooting: if you’re just starting out, advanced freestyle boots are too stiff, you’ll never bend your knees and ankles properly, you’ll never break them in. I think that was generally true of many older generation boots (say, before the early 2000’s), but not necessarily generally true for many current generation boots (exceptions apply, of course).
With respect to breaking-in boots, stiffness is just one factor. As you advance up the model line, the stiffness generally (but not always) increases. But break-in also depends on other factors, such as overall fit and extra design features: the more the boot initially conforms to your foot, the less break-in required. As you advance up the model line, you will generally get better fit and more design features, resulting in less break-in time.
For example:
(1) Your instep-ankle-shin follows a curved contour along the front. Lower models have one-piece straight tongues; requires more break-in to conform to the curved contour. Advanced models have two-or-three piece tongues stitched together to form a curved tongue; less break-in required.
(2) Your heel-ankle-calf follows a curved contour along the back. Lower models have a straight backstay; requires more break-in to conform to the curved contour. Advanced models have a curved backstay; less break-in required.
(3) Your ankle bones protrude. Lower models have flat sidewalls along the sides of the ankles; requires more break-in to create clearance for the ankle bones. Advanced models have pre-punched ankle pockets that accommodate the ankle bones; less break-in required.
(4) For deep knee bends, you need to flex the ankle of the boot front to back. Lower models have continuous sidewalls along the sides of the ankles; requires more break-in to flex. Advanced models have ankle notches; less break-in required.
(5) [Specific to Jackson] Jackson has found that many skaters have a narrow heel width relative to their toe width. Critical fit depends on a snug heel. Lower models use a single-width last; a snug heel can result in cramped toes; break-in may be difficult, and the toe box may need to be stretched out. Advanced models use a split-width last; a snug heel is paired with a wider toe box; no toe cramping, less break-in required.
And consider some design features that lead to more comfort from the start and reduce break-in:
(1) Tongue lining. The tongues of lower models are unlined or lined with thin fabric or thin sponge rubber; can lead to severe lace bite. The tongues of advanced models are lined with thick sponge rubber (1/2” or so); greatly reduces lace bite and hugs the contour of the instep-ankle-shin more snugly.
(2) Boot lining. The interiors of lower models have thin or no padding and thin or no lining; less comfort. The interiors of advanced models are heavily padded and heavily lined; more comfort.
(3) Ankle collar. The top edges of lower models are unfinished; they initially cut into your shin and calf until they break in and soften (which may be never in some boots). The top edges of advanced models are finished with a rolled and padded collar; much more comfortable and way less break-in required.
I grew up with the older generation (pre-early 2000’s) Riedells (the line has since been totally revamped): started with the 220, then went to the Gold Star, then went to the Royal. The classic Gold Star was infamous for being difficult to break-in; I (and most skaters I knew) complained about bloody shins and calfs (the current Gold Stars are much improved). About a year ago, I started skating seriously and started private lessons. I got the Jackson men’s Elite Suede (the Jackson men’s line and women’s line are slightly different; the men’s Elite Suede is roughly on the level of the women’s Elite 4200); this is an advanced model, just below their top-of-the line Elite Supreme; it’s rated for double jumps I’m concentrating on edges and spins; I don’t jump beyond half-jumps. But the Elite Suede took very little break-in because of the good fit and design features. If the Jackson line is a good fit for you, don't be concerned about moving up to advanced models when it comes time for your next pair.
Good luck with your new boots; and, above all, have fun!
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