I had troubles equalising when I first started. I found that I was rushing down too quickly and forgetting to equalise early enough. I now descend slowly and calmly and begin equalising as soon as my head drops. If you are equalising just before you feel pain it is too late. The water pressure will make it very difficult. I have also suffered a blood nose while scuba diving because I dived with a cold and suffered a reverse block on ascent. It damaged my right ear and I still have troubles equalising that ear. So be gentle and sensible when equalising. All the best.

I'm not experienced by any means, but you should be equalizing frequently (I try and do it at least once every metre - as recommended by a major scuba school with a four letter acronym, ahem), but not forcefully, and definitely BEFORE you feel the squeeze. If you leave it too late you might find that you actually cant equalize and have to ascend. Also dont forget that you need to equalize your mask aswell (by blowing air from your nose into the mask cavity). You shouldn't be using like swimming goggles as these cant be equalized and could lead to a feeling of pressure on your eyes - which may lead to permanent sinus damage.

You should definitely look into doing a free diving course (or even scuba if you're that way inclined), or at the very least go diving with someone who knows what they're doing. You will learn a considerable amount about human physiology in relation to diving, pressure at depth, effects of pressure, how and when to equalize properly and safely, etc. on these sorts of courses, and in my opinion is well worth the cash. You also get the whole "when not to dive" knowledge which really holds true no matter what style of diving you're doing.

My 2c