Matt I think you're on the right track with your idea to pre-pressurize your middle ear before you begin to descend. This is what I teach all my students to do, and I also tell them to equalize on every breath as they descend rather than waiting for pressure to build up. This way you are pretty much staying ahead of the pressure gradient rather than correcting it.
NetDoc mentions extending your neck to stretch the tubes, and along those lines I generally find that one ear clears more easily than the other so that if you stretch your neck and turn the blocked ear towards the surface, the micro-stretching and tension on the "bad" tube is often enough to let the bubble of air pass through it to the middle ear.
The first 20 feet are typically the hardest for equalizing because the pressure change is felt with a relatively small change in depth. I tell my divers who are having serious trouble with equalization to look at their computers when they ascend due to clearing problems, and to ascend just 20 cm (.2 m), try again, and then go up another .2 m if that doesn't work. I guess on a dive computer measuring depth in feet, .5 ft would be a good amount. The reason I advise pretty small steps is because the pressure change is marked at shallow depths, but also if you go all the way to the surface, you have to redo all the equalization over again that you might have already achieved successfully. That is, if you've made it down 10 feet and your ears are okay, but at 11 feet you are unable to clear, try going up to 10.5, making an attempt to clear and then re-descending slowly once you're successful. If you go up to 9 feet or 8 or 7, you just have to cover all that difficult distance again.
Finally, I'm also 59, and I take Claritin D (12-hour variety) the morning of every dive day. I don't have a BP issue (my BP is always in the range of 100-120 over 60/70), but I don't notice it raising my BP at all in a general way, and I only take it when I'm going to dive.