I've had a few Sony boomboxes throughout the years, which date back to as close as the early 2000's. A lot of modern boomboxes still hold up musically and audibly, but they're missing that "flair" that boomboxes once hold. Chrome accents, cool knobs, eye-catching meters, multiple radio bands, long antennas, etc. Boomboxes definitely shifted into a method of solely listening to music, rather than a statement piece or novelty item. Also, with the share of decent modern boomboxes, there are a PLETHORA of crappy boomboxes, which I'd say began in the late 80's because people didn't want to keep paying for quality.
To answer in short, a modern boombox is sorta pointless, seeing as there are many machines now that can do the job better and more efficiently. I just kept my Sonys for my nostalgia of 2003.