While we haven't lost any payloads we intended on recovering, we have sent payloads on one-way missions. For each flight we look at whether it is worth the extra expense and weight of a recovery-ensuring device (Iridium, Spot, radio beacon, etc). Sometimes we are just interested in the telemetry, such as with improving our tandem balloon flights, and the cost of recovery is more expensive than the hardware on a long-duration flight—they can travel large distances.
Your idea of increasing interest in ballooning by simplifying and selling a launch system is interesting. A couple of years ago I would have completely agreed with you. However, after spending the intervening time trying to create such a system, that also has altitude control, I no longer fully agree agree. I now feel that there are additional issues such as:
Expense of a flight: After factoring in lift gas, tracking, time, and recovery each flight is relatively expensive. I think most people are turned away by this cost, especially when this is compared to what it takes to fly a small UAV—charge the batteries, fly for a couple of minutes, then walk over to pick it up.
Steep and slow learning curve: There are a lot of different factors to consider when launching and successfully recovering a balloon flight. Some of this can be reduced with smarter hardware/technology, but most of it still involves due-diligence and pre-flight planning. And the feedback loop is not always complete after each flight. Did the flight fail because of factor A, B, or C, or perhaps some combination? It takes time and patience to overcome this.
Lack of interaction with the flight: For up-and-burst flights, all the interaction and control is done before launch. Then the balloon rapidly ascends and disappears from sight until which time it is hopefully recovered. Even with say our Boomerang system that has two-way communication and altitude control systems on-board, interaction is still through a computer screen filled with plots. The actual balloon is rarely seen, except for low-altitude flights which I find fascinating as a result. While I think this disconnected interaction can be acceptable, it boils down to what can you do with the balloon flight. Is the post-flight data, pictures, collected samples, or other results worth the effort?
That said, I do strongly agree there is a place for ballooning systems that simplify and reduce risks for each flight. An example would be our Doongara Balloon Cut-Down product—a pre-programmed line cutter that uses a burn wire to cut some line. The challenging part isn't the concept, if you can put together a Pi in the Sky then you can also figure out how to use some nicrome wire to sever a line. The challenging part was making sure it is reliable and lightweight. It took numerous test flights to refine the code and hardware, and we're still improving it.
So yes, I think there are devices and ideas that can help make HAB launches both more capable and more popular. While some people like the challenge of building their own tracker, others don't want to do that and instead just want to do X, Y, or Z. And if they can focus on X, Y, or Z then they will be more likely to fly a balloon.