Hi gryffin - just popping in to say you sound a lot like me! I was very anxious about diving, even though it was my idea (hah!) and I was the one who purchased our lessons & equipment as an anniversary gift for my husband in 2012.
I, also, have a ton of ear issues. I have tinnitus, so it makes me 50x more anxious underwater because I'm terrified I'll "do something" to make my tinnitus worse (it's already pretty bad). I continually have issues equalizing.
After certification, we immediately scheduled a cruise where we stopped in numerous Caribbean ports and we planned dives in each of them to get a flavor of various spots. With the exception of Curacao, all were boat dives. I felt like I was
more nervous about diving after the boat dives (in general) - not because we had bad experiences with the dive shops, dive masters or other divers - but because (1) my ears & difficulties with equalizing and try to "stay up" with the groups (2) I found out I experience motion sickness on dive boats (3) it all feels very rushed in trying to gear up and get the heck off the boat & it made me anxious (4) even though I was very clear we were novice divers, I felt like some of the dives were too advanced and that made me anxious.
We ended up doing a group trip the next year to Bonaire with our local dive shop and the experience was totally different. At first, we only used the house reef which was teeming with other divers, so we felt "safer" than diving alone. We branched out to shore dives with another couple and we never did a dive unless we all agreed on the location. We ended up even doing a few shore dives with just the two of us, which were a lot of fun. Last year we went back on our own (and did all the dives with just the 2 of us) and this year (next weekend!) we go back.
Shore diving really enabled us to take it slow, decide exactly what we wanted to do and not feel stress about motion sickness, feeling too rushed or diving a spot that felt too advanced. We get up when we want, go where we want, dive when & where we want and dive for as long as we want. In theory, I guess I should feel more anxiety since it's just the two of us - but overall, it's less stressful. Also, I seek out spots where a few other divers are to help combat anxiety about being totally alone.
Also, I ended up buying some vented ear plugs that help with my ears a little and my husband understands I have to descend slowly, he's totally fine with it. I've found that looking up (towards the surface) as well as moving my head (slowly) side to side (head to shoulder) assists me in equalizing, and I also always equalize on the surface, as soon as my head is underwater, and many, many times while under. I was also getting super stressed when I couldn't equalize and thought I was trying too hard at times - so now, I just relax and signal my husband that I cannot descend any further, or that I have to ascend a little, until my ears cooperate. It's a lot of reminding myself to relax, equalize early, often and gently and to take it slow.