Hi Keats,
There is a lot of good information on the basic process already available on this site and from the many videos on the internet so I’m just going to mention the high points. Some wood is just stubborn. Species and grain structure makes a huge difference in how you have to approach the work. That is why traditional woodworkers have developed scrapers, toothed blades, and high angle frogs. I doubt that your sharpening is the cause of your issues.
First thing to consider is the stock itself and I would recommend you practice with some straight grain material until you get more experience. Details like rising and falling grain, figure such as curls, crotch, and birdseye creates special circumstances that are considered advanced and should be attempted after the basic skills are mastered. I don’t know the condition of the stock you are starting with but I am assuming that it is just basic rough sawn or machine planed stock and will start there. Make sure that you do remove any wire edge that might remain on your blade, set the chip breaker close to the edge (after you tune it to fit properly of course) and make sure your plane mouth is relatively tight ( on the smoother)to minimize tear-out. The #5 is normally used as a true jack and can be used to do the rougher work if it has a slight camber and needs wider (than the smoother) mouth to pass the shavings. It is a two step process with the jack doing the basic shaping and the smoother doing what the name implies. I normally use a flat, or minimal camber on my smoothers and just round the corners to eliminate plane tracks. Others prefer cambering the smoother and if you prefer that method I won’t argue. Do use a straight edge and winding sticks to establish the areas that need to be reduced in order to make the face into a flat plane(geometrically speaking). Later on you learn to use the plane edge to function as a straight edge in some applications. Be sure and hold the stock secure to prevent movement but don’t use so much pressure that you distort the stock. You want to be able to work the entire surface without damaging the tools and you might need to shim the stock to prevent rocking. Keep in mind that you are hitting high parts of the stock most of the time instead of running shavings the entire length of the board and much of the work may be limited to specific areas at this point.
The work with the jack should leave the stock flat but not “smooth”. With straight grain stock, this should have left you with a minimum of tear-out so that the smoother only needs to take off the high spots from the previous work. You should then gradually (finely set blades take thin shavings) bring the rough surface down to the desired degree of smoothness but you do need to keep in mind that overly aggressive smoothing can throw off your flatness and that aspect of your work should be checked repeatedly with the winding sticks and straight edge. The good news is that a finely set smoother should only be removing about 1 to 2 thousands of an inch with each pass. Again, you can restrict your passes to trouble areas and there is no requirement to do passes along the entire length. You can skew the plane, make “circle passes” when working isolated areas, or can reverse the planning direction for rising grain. Don’t become obsessive over the quality of the shavings in the process. It is the surface of the stock that matters, not how pretty the shavings are. Later on you will learn to “read” the shavings to help diagnose what the plane is doing but that will come later. Lastly, get and learn to use a scraper.
One thing to keep in mind with “traditional” woodworking is that many surfaces in old pieces were never worked with a smoother. Some surfaces such as undersides of drawer bottoms, insides of table rails and back surfaces of cabinet back boards were left straight off of the jack and fore planes. The “old timers” were often working under pressure and left the finer work to surfaces that were for show or where it was important to have a better surface for reference for other operations. Their experience told them where it mattered and where they could cut corners. It wasn’t considered poor work because it didn’t change the appearance during normal use and didn’t affect the strength of the piece. It was the standard of the work.
Have fun.