That summarizes my concerns nicely. Improvement is continual, until it peters out because the company's attention shifts to newer products. Where is the SDS2000X+ on that curve?
Your concern is your prerogative.
Products are supported until there are no bugs to fix and platform cannot accept new stuff.
Where is SDS2000X+? Still in the active support, like we already said.
I have never said improvement is guaranteed. No A brand improves their products unless they are really forced. And then only for newly bought product. For instance, on Keysight 3000T if you bought full bundle, and later Keysight added new protocols, you would not get those. You have to buy them separately.
As example of big chunk of development I will mention rewrite of part of acquisition engine to support filters that were not even in the stars when platform was devised. Since you do understand the complexity you'll get my meaning.
As I said, Keysight's last release of FW for 1200 Series was 2 years ago. Same as R&S RTB2000. These scopes don't have a fraction of functions SDS2000X+ has. RTB2000 is a bit closer for 4x the price. Nice scope though.
There is simply no reason to release anything on predefined schedule. Nobody does that. And releasing some trivial things just to be able to say you released something is something that is being done for software products on rent/lease/subscription. And is done just for reasons to justify why people are paying for subscription. No additional quality stems from it. Quite the opposite most the time. Kudos to those exceptions that still do the good job despite.
As for competition and other models, they all have a place under the sun.
Rigol DHO1000, apart from 12 bit is otherwise simpleton scope in comparison. New SDS1000X HD will be class above.
Rigol DHO1000 MSO is a figment of imagination of Rigol fans. There is not a peep of anything like that on horizon.. not even a rumor from China...
By that logic it is never the right time to buy anything. There is always some new, prettier, shinier, glossier, more fancy product just few months away...