Here's a delicate question.
Before computer modeling (and computers for that matter) how well could a skilled designer predict that outcome of a cabinet without building numerous prototypes?
I can't speak for the pro's, but for us DIY'ers, we're living in a golden age. Perhaps beyond anyting else, there's the information that's available on the Internet. Also, decent modeling software is available for free and runs on any computer, including your phone.
When I built my first speaker, all I had was one book from the public library, and the formula I needed to use was wrong. (The units of measure didn't work out, that's a clue). Also, I had no access to information about how a bass speaker might differ from a hi-fi speaker, etc. And no way of testing anything.
Today, I can read about speaker theory online, I can find a spec sheet for any driver on the market (if it's a legitimate supplier), and even some of the measurements are starting to be democratized thanks to PCs and their audio hardware, as well as auxiliary gear becoming affordable such as high quality multimeters. We still have a long way to go before DIY testing can produce results that are believable for widespread consumption, but they can be useful for troubleshooting and verifying design assumptions.
It's my guess that new components such as neo drivers are more DIY friendly, because for many of us (including myself), we can easily buy more performance than we really need, and not worry about squeezing every last dB out of a design.
Glue has gotten better.
On the negative side, there's also a blizzard of false information and folklore to wade through. That's not unique to bass speakers. I don't know how you can reliably separate truth from crap on the Internet without being a physicist and mathematician, because I've never had to do that.
Short of actually designing cabs and cutting plywood, the same golden age applies to being a sidewalk engineer and just enjoying the conversation and new design ideas coming out.