Some really 'crappy' steels are a PITA to sharpen, simply because the grain size or structure, or hardness (too soft or too brittle), won't allow them to take and/or hold a fine edge. More often than not, that all comes down to heat treat issues, and not necessarily the type of steel itself.
I'd say a 'crappy' steel (as
perceived by type only) that sharpens up easily, and hopefully holds a fine edge reasonably well, really isn't so 'crappy' after all. That's what knife steel is supposed to be. A knife steel which sharpens easily, but isn't wear-resistant like many modern 'super steels' (the alleged 'good' steels), isn't actually bad, it's just living up to it's design specs.
Ease of sharpening is mostly about knowing what abrasives work well for a given steel. Higher wear-resistance due to vanadium carbides, such as in S30V for example, can be made 'easier to sharpen' by using abrasives that'll handle the carbides well (diamond, CBN). Middle-of-the-road steels with moderate wear-resistance, like 154CM, 440C, D2, etc. respond 'easily' to aluminum oxide and silicon carbide (and diamond/CBN, but they're not necessary). Simple low-wear steels like 420HC (wrongly perceived as inferior, much of the time) or 1095, are usually easier to finesse with gentler abrasives like natural (Arkansas), aluminum oxide or even silicon carbide. If using harder abrasives like diamond on these, it's easier to control the process using finer grits, as the coarser-grit super-abrasives will be overkill, most of the time. That 'overkill' means it's very difficult to refine edges, which in turn makes sharpening these 'simpler' steels 'not so easy' anymore.
David