Back in the day, when I had a 1400, and then a 2400, the biggest advantage of 8.6 was improved power/battery management. Many of us saw an increase in battery life over 10% when we went from 8.1 or 8.5 to 8.6.
If you are running off AC power, then that won't be too much of a big deal. There really is not much you cannot do in 9.1 or 8.6 that you can't do in 7.6.1, especially if you use SpeedDoubler for the copying improvements. Of course, there will always be the odd program you need 8.x or 9.x for...