And I can see how for most businesses that might be true, or at least much more comfortable.
However, for certain products it just does not make sense to have a recurring cost (I have in mind a desktop utility someone might use a few times a year)—although charging for a major version upgrade may be possible.
What I'd like to read but can't find is something like: "What you'll wish you knew before starting a one-time-cost/pay-to-upgrade software business".
If anyone has general comments about this (on both negative and positive aspects would be great) or resources they could point too, that'd be much appreciated!
I doubt desktop software is coming back. If you can make it a website and accessible over the web then that will always beat desktop software. The only exception I can imagine is something like multimedia editing which requires access to actual hardware for crunching numbers (coding and decoding audio and video). Everything else can run in the browser these days.