This is user forum. No one here can answer on your questions (and you probably understand that, so why are you asking?)
If you have payed for all versions before, $99 offer was one year ago. For the Lifetime (could be perceived as paying in advance for this year). If it was $199, you have skipped/waited too long initially with Platinum. If you do not see the value, why you want $99 offer now?
Some users have payed just to support the company they like, other because they like the product, probably someone because he/she was always doing so. Everyone can have own opinion and reason. And the value of $99/$199 is different across the world (for some people that is monthly salary, for other 1-4 dinners...).
Note that I personally (unfortunately) agree with all your technical statements... But they have promised to improve (confirming some mistakes! something I rarely see from companies). And that is a matter of trust/believe they can. Is that going to happened? When? How? We (users) do not know. And that is naive to expect someone from Cakewalk will come here and explain you everything in details.