Slow down......breath.....
Okay, hand stitching simplified: The needle size you need will depend on the thread size you use - because of the size of the eye. Now that that is covered, stop buying the big eye needles from Tandy. Go to Walmart's craft section and look for a pack of needles that has 6 or 8 needles in it, two each in four sizes. The whole pack, last time I bought one, was around $2.00. You want the smallest eye you can still get the thread through, so that you stop breaking the eyes. BUT IT"S A SHARP POINT.....yeah, it's a sharp point right up to the time you run a sharpening stone or file across the tip.....then it's a tapered point . When I hand stitch items, I use waxed linen from Hobby Lobby and the two smallest needles in this pack.....I also use them for finishing stitches I make with the BOSS. When I get to the part where I'm back stitching, I use needle nose pliers to get the needle and thread through the hole - short straight pulls, using my thumb on one hand to push the pliers....no big arm movements. You might need to change awl sizes, depending on what you're stitching with, because at a minimum you'll be putting the needle and TWO thread diameters through the hole. On a back stitch, it's a needle and FOUR thread diameters.....which is fine because you're using friction to keep the thread in place.
It's not as complicated as your perceiving it to be...just match the needle to the thread, and use the appropriate sized awl.