Ya know, a radio could be created which is simple for casual users who never want to touch a computer, and may only really be interested in simplexing with other GMRS users who may or may not be using the same equipment, but at the same time give it the capability to do more advanced things via programming software like:
Repeaters of same frequencies but different tones
Repeaters with split tones
Scan out of band (e..g. 2m/70cm HAMs, Police, Fire, etc)
DTMFs per channel
Power level per channel
etc etc
Such things could be hidden behind an "expert" menu from the keyboard, or even ONLY programmed via computer software (Mac, Linux, Windows, etc).
That being said, @pcradio mentioned "CHIRP is not much better" ... Well, I've got to say it is worlds better than the Wouxun software for KG-935G! While CHIRP has its frustrations, the Wouxun software is absolutely horrendous as far as the channel memory editor is concerned. I have some 10 year old LED Sign software which looks like WindowsXP with menus completely in Chinese, but it is much easier to use than the Wouxun KG-935G software. But there's a wait-list for Wouxuns, so nobody there sees any benefit in fixing/making-usable their programming software.
I've not checked into RT Systems software, but with a proprietary cable, and no trial system that I can see, I'm not sure it is any better than CHIRP. Plus, it does not support some of the weird radios I have (which are supported by CHIRP). Until a radio manufacturer produces quality software to program their under-$200 radios, CHIRP is the way to go. So, not counting RT systems, here's how I see it:
horrible factory software
frustrating (but consistent) CHIRP
wonderful factory software
#1 is the norm, #3 I've never seen. So focusing my effort on #2 (CHIRP) is the forced compromise. It provides a fairly consistent interface across radios, so I don't have to learn the unique design quirks from the various software "engineers" at Baofeng, Retevis, Wouxun, etc. (Why, for example, did Wouxun choose to put the channel label in the 11th column, way over on the far right of the screen, vs CHIRP which puts it in column 2, on the left side of the screen, right next to the frequency, and one hop from the channel number? Why?? WHY??? And "Hello: Copy/Paste" from another program like, I dunno, Excel? Nope, sorry.)
ETA: (I forgot to mention before I hit SEND) It wouldn't seem unreasonable to me at least that a manufacturer couldnt release a "basic" radio for under $100, but sell an add-on "subscription" (if you will) for another $50 to provide great programming software to unlock advanced features and/or long-term support. Missed revenue opportunity on their part I guess.