Technology made huge leaps from the 80s to the 90s. Our cell phones in the 90s did one thing: made calls, but we had them. We had email and the internet, even if it was slow as molasses dial-up. Digital cameras existed, but they were very expensive, so most people still used film, but they existed. TV was in color, and most households had at least two. Cars were built to be aerodynamic, not stylish (I drive a 1994 car, and it doesn’t look that different from other cars on the road). DVDs existed, although since DVRs didn’t, people still used VCR to record shows, so most people hadn’t made the switch.
None of those things existed in the 80s. People who really needed to keep in contact carried pagers, and when they went off, the person needed to find a pay phone. Computers still used floppy disks (5.25"), and most computers were sort of glorified typewriters. People used them for word processing, Quicken, and spreadsheet databases (like Excel). Some people played games on them, but they were either really simple, or had to be loaded from several disks. There were programs for making calendars or cards, if you had a bubble jet printer, and a (very expensive) scanner.
Going from 2015 to 1995 would be much easier than going to 1985-- not just incrementally easier, you know, like only 2/3 the burden, if you tried to quantify it; the extra 10 years would be more than 1/3 more of the burden. By the same token, I think that for someone born in 2000, who in 15 next years, there wouldn’t be that much difference between 1985 and 1975.
A lot would depend on whom he met. People adapted to technology differently. My parents did not have a VCR until 1987, and didn’t have a color TV until 1992, or a CD player until about 1998. They have never had internet in the home, although they had it at work in the 1980s. My mother didn’t get a cell phone until about 10 years ago; my father passed away before they were small and cheap.
My aunt and uncle, on the other hand, had color TV in the 70s, a VCR from about 1982, cell phones in the late 90s, a CD player practically as soon as they were available, and internet back in the AOL days.