The 'old school' way -paid upgrades, free updates- works just fine. Updates are free, upgrades are charged for ... it's an accepted and proven system.
Selling a RED2 upgrade to a 'RED for Business' or 'RED Personal' user won't get you $199 for each and every single licence, but $69
(when upgrading from RED for Business), $129
(when upgrading from RED Personal) or $199 instead. But those for who current proposal is a deal breaker will stay onboard.
Get the current (and new) users to also go for the CC RED2 Mail service on top of purchasing a licence. It's added value. Get it to import exported lists from the competition, make the transition easy and appealing." Treat RED2 just as it was RSD2, but offer/sell the optional mail service additionally.
For those who don't need the CC mailservices itself and rather stay with their current (and proven) mailservice like MailChimp it's just the RED2 app itself they will need (or want) to upgrade. And pricing? Well ...
RED2
RED2 : $199
Upgrade to RED2
You currently own RED1 Personal : $129
You currently own RED1 for Business : $69
Additional/optional service (the added value)
RED2 Mail service : $9 Monthly plan* / $89 Year plan
*montly cancellable, auto renewable
– Richard
Living in Zevenbergen, the Netherlands
13" MacBook Air M1 + 2x LG 24" IPS QHD / 8GB RAM / 500GB SSD / macOS 14.3 Sonoma