In the event of Lone Wolf not being able to support HLC or being dissolved, just as with other programs, like old DOS games and such, HLC can drop into being orphan software, and have legal means to subvert or remove the license mechanic.
Now, likely Lone Wolf will do this on their own for their users, having the license revert to an always on for the user, much like the old CD keys for past programs being phased out.
The problem that the user will have and is the biggest huddle is the licenses that the program contains of the various game systems. These will lapse, and though the information will still be on the computer, updates and bug fixes will fall to the user community and the situation like what happened to Etools may result.
There are some that still has Etools around, though using it for Pathfinder is likey nigh next to impossible, and other licenses isn't something it was set up for. (Code Monkey was working on a newer, better character generator, but life happened and it is unlikely to be released)
This newer model of an App, being an online portal on a browser, is completely dependant on the company keeping things running. The worry and fear is that the information isn't secure or that one will not be able to access the character at a point when it is needed. It also expands the parameters of the original program, making it into an online GM tool and character generation seems to be secondary to the overall use of the App.
Realtime adjustments for in game changes such as spell buffs or being under a condition is something that is nice, if your not using Pen and Paper to run the character. This interaction started with the Ipad App that used/made Por files and is basically the same program as the PC version, but one could do adjustments on the fly on the device.
The main difference between the Ipad version and the HLO App is that one has to be online for the newer iteration. This presents a problem for one trying to use it in a setting where internet is spotty or not available, such as most convention settings or in a gaming store. The offline mode still needs the character to have been loaded up, as there are no files to bring up like with the older app and HLC program.
Overall, I believe in Lone Wolf and think they wanted to provide the best possible product for us to use. The move to an online app instead of an actual program is indicative of the times, where cloud computing is the wave of the future and devices are slowly replacing pen and paper. Hopefully, there is some thought to having a way to save characters locally and some sort of reader for offline use. Much has improved with the character print outs and the information presented. The plug ins for Society play and boons is still a work in progress, i believe.
The older program (HLC) is still there, and we can use it. Newer systems, though, are not forthcoming for the old dog. The new shiny App (HLO) will do more than the old program could, though whether or not the user wants all the bells and whistles or just the character generator aspect seems to be the barrier for the old users of the previous program.