HL also hasn't changed from when it was first brought out. And even when it first came out, it was already a very dated and clunky interface.
Community packs shouldn't be a measure of a paid for product either. Relying on the work of unpaid volunteers as part of your business model isn't exactly what I'd call ethical. The fact that they haven't been able to get a license while Curse, FG and Roll20 have, is also telling.
Hell, the only reason I dropped money on HL was because FG was too expensive, I had no desire to use a VTT for character generation and homebrew, and nothing else existed to fill the niche I needed.
Now that there's genuine competition, all of a sudden we see LW looking for an UI designer. Too little, too late. Then again, they've already got my money so it's not like they care.
Though I couldn't care less about 5e or Wizards, I ditched them long ago, with no chance of turning back. Your post strikes me in an odd way.
There have been many character tools like HL along the way as traditional Pen and Paper RPGs transition to the digital age, only slightly faster then the Athabasca Glacier.
Few of them are still here today, HL being one of them.
You also make a great point, HL is reasonably priced for a dedicated product, offering one thing, character management. In a nutshell you have actually helped its position, the opposite your posts would have me believe.
Though I agree HL UI is clunky, it is also the best over all character management tool I have used to date. It is also one the best Tactical Consoles, as it is so well tied into the ability to its character management tool that can be used for encounter management. You must also see this, or you would not be here, or owning it. Though of all its components, the Console could use the most "refreshing".
Though on going it can seem costly, but no more so then buying all the books is. In fact, if you buy PDFs + HL it is very close to the same cost, enough so its a push, and saves a few trees along the way.
LWD has had and will always have some competition, but unlike Code Monkeys which I was also heavily invested in, LWD is still here, and expanding its product base, not shrinking it. Realm Works is a great product and extension of the digital age finally arriving for RPGs, but its also separate, not buy it all or not at all, we have here a choice to buy into either or both. You can also buy only what you need, as you need it.
The idea that HL UI was to be improved has been spoken of here for some time, but it was also evident that until RW was ready for general market place consumption, that was in the future. Hopefully the job posting is an indication that future is now going to be a reality.
Digital RPG tools is a small niche market, no Microsoft or Apple here. So it should be understood that we are not going to see an overnight revolution, but small evolutionary steps. Hell even man didn't just get up one day and walk away from its home in the sea.