This has been my experience exactly. V1 was custom built for a single client and they loved it. As we tried to expand to multiple clients the v1 was too narrowly scoped (both in UX and code architecture) so we did a full rewrite attempting to generalize the app across more workflows. V2 definitely expanded our client pool, but all our large v1 customers absolutely hated it.

We never did a full v3 rewrite, but it took about 4 years and many v3 redesigns of various features to get our legacy customers on board.