Handstands are hard.
There are many other skills I've been able to practice piecemeal, dabbling when the mood strikes me over months or years, and still seen noticeable improvements (QDR being a great example). Handstands are not one of those skills. While I've technically been practicing handstands for years, the best I'd ever had was maybe a ten second freestanding handstand, which was a total fluke and unrepeatable. In parkour there's a phrase: "once is never," thus as far as my handstand went it was never.
I've written before about the motivation for movement, making the pursuit fun and playful. For myself, at least, that's difficult to do with handstands; they just take work. Logged hours, brutal drills, and progress slow to the point of being hard to see at all, in a position that's the opposite of innate, with your feet completely out of communication with the ground...all the ingredients for a skill that's more comfortable to quit than to persevere and triumph.
Looking back now I'm not surprised I never invested the time to properly learn the handstand before now. It wasn't valuable to me, when compared against all the other skills I was already working on. A handstand is just a cool party trick unless you've got a purpose for it. While there are many excellent benefits to learning it from a movement intelligence perspective—better alignment, improved shoulder strength, greater body awareness, and being comfortable upside down—those benefits were only intellectually interesting to me. I didn't feel a tangible desire to learn; it was too abstract and distant at the time. It wasn't clear how it would help either my parkour or martial arts practices, and even once dancing entered the picture (where it could conceivably be useful and interesting) I still didn't feel compelled to do the work to solidify the skill.
I was curious about the handstand, at some level, but it was a passing curiosity, not sufficient to move me to commit to a consistent practice.
Then I discovered the local circus and acro yoga communities. For me, being able to balance myself on my hands, just for its own sake, wasn't enough. But if it meant being able to work on higher-level skills to try with other people, well, that was my ticket to physically desiring a better handstand.
It helps that many of the partner acrobatic skills that have you balanced while inverted are easier to hold than an actual freestanding handstand, so I was able to experience what balancing upside-down felt like. Plus, with knowledgeable folks there to correct and teach all the subtleties of the handstand position, progress has begun to feel less sluggish.
In my case, the path to enjoying the process has been to focus on making improvements towards a handstand press, which is addressing my weak point in the ability to pull the legs up from the ground while keeping them straight. Handstand line drills are still maddening, as is learning how to sense the ideal hollow position, but it's all feeling more worthwhile now that I have both a community to make use of the skill and the neccessary feedback to improve more quickly.
Once I found a purpose for the skill, backed by a community, the desire coalesced into action.
Update: but work and life has taken me further away from those specific communities, and the ideal spaces to practice, so handstands have yet again fallen by the wayside priorities wise. I'm nursing a hamstring pull right now though, so it may turn out to be a good occasion to re-introduce them along with more upper body centric skills to keep the temptation to do things which strain the hamstring at bay.