They are trying to get as close as possible to the amount people are willing to pay before leaving - and they figured out how to do effective vendor lock-in - reduce onboarding friction, give away free credits in the start, price migrating out to oblivion, etc.
I don't really see how this will improve - new competitors will try to emulate the approach to reach similar margins, budget providers won't have the capital required to commoditize SaaS offerings.
This could work if you have people that know how to operate your server. I guess that it is not the same if you have your own rack in some data center and AWS servers. What about routers, networking and all of the other things?
Basecamp doesn't have a cap on file size or count, as well as storing every version of a file, in full.
They also have an email service (Hey) now with no cap on attachments. (If they're too large for the receiver's SMTP server, they just get a link instead, to a file stored on Hey.com)
Give agency folk an infinite file-hole to throw .PSD and .afdesign files into for 20 years, and commit to never shutting down any product ever (There's still clients on Basecamp Classic and Basecamp 2!) you end up with BIG disk space requirements.
I don't really see how this will improve - new competitors will try to emulate the approach to reach similar margins, budget providers won't have the capital required to commoditize SaaS offerings.