> Yes, I agree that this is the fate of most. But I refuse to believe it's inevitable
Yes exactly. It is not inevitable, I’ve worked on several “enterprise” software suits that did not suffer from this problem. However! They all had that period in their history where they did, and this is why:
Early on in a companies history there will be a number of “big” customers from whom most of the revenue is coming. To keep those customers and money flowing, often bespoke features are added for these customers and these accumulate over time. This is equivalent in character to maintaining several forks of an OSS project. Long term no forward progress can be made due to all time ending up in maintenance.
The solution to this sorry state is to transition to an “all features must be general for the product” and ruthlessly enforce this. That will also mean freezing customer specific “branches” and there will be a temporary hit to revenue. Customers need to be conditioned to the “no bespoke features” and they need to be sold on the long term benefits and be brought along for the ride.
This then enables massive scaling benefits, and the end of all your time in maintenance.