Dan,
Clearly you were able to play courses designed in 1985 with a 1985 era Titleist DT in 1985, right? You seem to be worrying that you'd have trouble with courses designed in 2005, which were built with the new technology in mind and are assuming golfers now hit it further or have greater carry than in 1985. So what's the problem with moving up on such courses that would be assuming you have capabilities you may no longer have if the ball is rolled back?
Realistically, I'd expect some courses would adjust their tee locations and yardages to compensate. Some back tees would be closed and abandoned, some regular men's tees would be moved up to the senior tee pad, etc. A few long par 4s might become short par 5s, particularly the long par 4s that used to be short par 5s 10-20 years ago.
How many sets of tees are on the course you refer to that you currently play the next to back set on? If there are five sets, why would you have an aversion to moving up to the middle tees? If technology had been static for the last 20 years, and you hit it the same as you did in 1985 (actually you'd hit it shorter, since you are older now, but I'll give you the benefit of the doubt) do you believe you'd still be playing the next to back set of tees?
I played a course a few years ago that measured 7510 yards and was essentially at sea level (maybe 400-500 ft elevation) and I played it with wet fairways. There's no way I could even remotely contemplate playing such a course with 1995 equipment, let alone 1985. If the ball was rolled back and I returned, and for some silly reason they left those tees the same length, I'm sure as hell not going to feel any false pride that would stop me from moving up to the next set of tees!
I'd just follow my simple rule of tee selection:
If you are hitting mostly fairway woods for your approaches, move up. If you are hitting mostly wedges, move back. Anyone who has a realistic idea of their driving distance can make a pretty good guess as to what tees they should play just by looking at a scorecard and seeing the yardages of the various holes.
Maybe there needs to be an '*' on that for crappy designs with lots of forced carries where you don't have very good odds of making some of the carries during common/typical weather/wind patterns.