The sump plug is usually situated at the lowest part of the sump, although there might be a little trapped behind the internal boss of the plug. A pump through the dipstick hole will only remove what is in the sump, and only get the same amount as removing the plug if the tube can get to the lowest part of the sump. The dipstick is rarely above the lowest part of the sump, so getting the pipe low will involve a bit of luck.
There will be some oil 'trapped' in oilways and the cylinder head, which is why the book will usually give two figures, the total capacity, and the oil & filter change capacity. I think the only way to get more out than from the sump plug would be to remove the cam cover and mop out all the trapped oil, then try to vacuum out the oilways.
The oil has a job to do to carry any soot and particles around and deposit it into the filter. Some heavier stuff may collect in the bottom of the sump, where draining is likely to be more successful than pumping. If the oil is regularly changed, as specified, the trapped oil will do no harm, and has been done this way since the engine was invented. I can't see a pump doing a better job, but is in this case useful when the plug is damaged.