I think one of the secrets of freehand sharpening is developing a way of holding the plane blade securely so that you maintain the honing angle, so that the blade doesn't pivot up and down, rounding off the edge. Everybody develops a slightly different technique, so this may not be ideal for you, but I offer it for what it may be worth.
When gripping the plane iron, I support the bevel side of it (which is underneath as you hold it to sharpen it) lightly on my thumbs, and rest the top end of the blade in the webs between my thumbs and index fingers, then apply pressure to the upper (flat) surface of the blade with my index fingers. My thumbs and index fingers are just clear of the surface of the stone, so are about as close as I can get them to the cutting edge without dragging my fingers across the stone. Then I feel for the grinding bevel of the blade on the stone, settling the whole bevel in contact with the stone. Then raise it a couple of degrees so that only the cutting edge is in contact, and lock my wrists. Then, with pressure from my index fingers (and second fingers if the blade is wide enough), start honing by pivotting at my shoulders and elbows. My forearms stay horizontal, and parallel to the bench, and I take a firm stance with my feet, and keep my head still. This feels awkward at first, but with a little practice you relax and just stroke the blade up and down the stone. It quite quickly becomes second nature.
The real skill is ensuring that the blade you're honing can't pivot about the cutting edge on the stone, as that will round the very edge. It's OK to round the bevel BEHIND the cutting edge if you want to, but you must NEVER exceed your chosen honing angle right at the edge. Once you develop a technique that suits you to hold the blade so that it can't pivot above the honing angle, you've just about cracked freehand sharpening. You'll get better and better with practice.
There are a couple of ways to see if your finished edge is sharp, once you've honed and backed off the wire edge. On is to hold the edge up to the light, and look for a gleam of light along the edge. If there is one along the edge or part of it, that's light reflecting off a rounded edge, and the blade isn't sharp. If there's no gleam of light, there's no rounding, and the edge is sharp. Another test is to (gently!) feel the edge with the ball of your thumb. If it catches your skin, it's sharp; if it slides over your skin, it isn't. Another is to rest the edge on your thumbnail. If it catches, it's sharp; if it slides, it isn't. Using one of these tests can tell you whether you need to do more work to the edge without having to reassemble the cap-iron, reset the blade in the plane and take a test cut.
After several honings, the sharpening bevel you create on the stone will start to get larger, so will take longer to bring back to sharp. You can either lightly regrind the primary bevel (I use a Tormek wetstone grinder, but some people use high-speed offhand grinders, or a very coarse grit sharpening stone) or slightly increase the honing angle. Obviously, there's a limit to how much you can increase the angle before regrinding becomes necessary, but it can help you finish a planing job without having to stop to regrind. It's not really best practice, though.
Keep on persisting with the freehand sharpening if you can get it to work for you; it's a handy skill. However, if you really can't get on with it, there's no shame in using a honing jig. The only 'shame' is in having to use tools that are not sharp enough!