Exactly, that's the core of the issue: it is very easy to overestimate the advantages of the new design/rewrite. But even worse very easy to underestimate the advantages of the old design. Because in a bad system (the ones you want to rewrite), things are generally not that well specified.

That's also defines what may work as a rewrite and may not work: if your application has a lot of external dependencies, and is used by customers in a very tightly way, rewriting it will take forever unless you don't care about losing your existing customers (because you lose what works and what does not). What makes matter worse is that you are more likely to make those mistakes early in the business.

If your application does not have tight integration with the customer, then it becomes much easier to replace it, one part at a time. Otherwise, you are likely to just recreate the same monstruosity anyway once you managed to support half of the features from the old version.

I think rewrite make sense in some cases, but the natural reaction should be don't, especially when you don't have that much experience. Successful rewrites are the exception, not the rules. To make a dubious analogy, that's like the junior programmer would think that his bugs are actually in the libraries/compiler he is using. The senior programmer knows it is almost always his own fault, and the very senior one has a few stories about long night debugging caused by compiler bugs in the old times.