I think most of us have found that sharpness is a magically dynamic, ever changing state of learning. You start off with an idea of what sharp is, in common sense terms, but very quickly, you'll read something or some kind old timer will show you something really useful, that you didn't know before and your sharpening skills will just 'click' up to the next stage.
From my personal experience, i often can't believe the level of bluntness that i regarded as 'razor sharp' in the early days of learning how planes work. My first flea market Stanley No.4 could have rivalled a cricket bat for its cutting incompetence. At least for the first year i didn't even try to sharpen. If it cut wood, then the plane was a plane to use, if not, then that plane was of no use.
Initially, like most people, i tried those bottom of the chest coarse oilstones which were never flat and had been clogged with 100 years of grime and graft. Sufficed to say, much tearout, lost temper and frustration at not knowing why this darn thing wouldn't work properly. The big leap from essentially blunt blades came for me, when i read David Fink's superb reference on making planes, which i believe is the best available, general course, covering all aspects of planecraft. That book layed out in simple terms the absolute prerequisite, which says, either you get a consistently angled burr and a flat back, or you have a poor edge. A fingernail to find the burr on the back of the blade is in all seriousness probably the most useful sharpening tip i've learnt in 10 years. Before that, i didn't really 'get', that often, i wasn't actually reaching the edge at all, but just honing the lower part of a convex bevel. The oilstone sharp blades moved the edges from being totally blunt, to a reasonably useful cutting condition, but still with much roughness and patchy bevel angle.
Eventually sharpening only by hand using the side to side method achieved much better angle consistency. This great technique was learned when i bought a Steve Knight jointer. My formerly lofty ideas of sharp were destroyed in seconds. His website has some great tips for the eager novice. I still judge my sharpness against the out of the box sharpness of Steve's planes. However, with the hand method, i was still rocking the blade a little, which rolled the cutting edge and detracted from the final sharpness.
The next step up, which really made the biggest leap i've seen in edge performance, was when i bought my first Japanese waterstones. Firstly the back flatness was shockingly exact and what really converted me was how quick they are. I found that the coarse/medium stone by King to be unbeatable value for money at £15, though that was a while ago. In the early stages, i often spent 5 hours trying to hand hone the chips out of a rock hard 19th c. Ibbotson or Hearnshaw Bros. iron. Many times it wasn't successful. With waterstones, i could use the right grit and have a totally butchered blade which hadn't been used in a century perfectly dressed in under an hour. The 6000 grit is the most impressive thing i've seen in a while, which for the first time got me to a razor worthy edge. My test at this stage was,'did it take a hair' and did it cut a piece of writing paper, without tearing or having to skew/slide the blade? You've got to keep them flat and deglazed for the best results, but they are superior in terms of paying for themselves and the top level results they bring.
Just when i thought that i had finally 'arrived' in the sharpness stakes, i bought a Scheppach electric wetstone, which has a gradeable wheel, running in water and a leather honing wheel. In the first few days i was shocked and endowed with many painful but much appreciated hand cuts. As is the way, what i thought was sharp, turned out to actually sit somewhere at the low end of the newly discovered razor sharp scale. The Scheppach gets a honed edge far more consistently crisp, with none of the common roll which knocks back the edge, when you sharpen side to side by hand. The test i now use employs hitting the blade against the edge of newspaper. I have found that a waterstone edge will only cut a limp sheet when it is perfectly hand honed, but most often it will bend or tear it. With the jig held leather wheel hone, you know the edge will stand, when it will, without effort, pass through a page of thin newspaper from top to bottom without any buckling or tearing. I find that test will accurately tell me when i need to re-hone the plane blade, long before you start screaming after tearing out your best board.
Sorry for the long essay, but i know that i for one would of jumped at the chance for a few tips in the early stages, when my workshop was a truly dangerous place to be if you were a piece of wood. Cheers, Nick.