Can't answer the specifically "Drupal" part (as for me I once had a certain pressure behind me to use it, found it atrocious at the time and won't look to repeat that; if their software is much better / much more to my taste now, good on them). But in principle, at least from a certain app size upwards, I'd rather start with something working in principle, then improve on it.
That said, it might still be more difficult to get things right with Drupal than with some other softwares where you have better continuity between versions. At least traditional search engine results tend to handle version changes rather poorly meaning you'll get tons of advice that don't really apply anymore because they're years old. That happened a lot to me when trying to help out a friend with a WordPress installation.