If you're going to go for it, my suggestion would be convert up to a fully mechanical shift. I've been running my electric shift for 5 years and have had relatively little problem with it. There are several fella's on the boards who keep Stringers going and all of these drives are 30 years old plus. Overall, they're a pretty robust system - but they have a few "Achilles Heal" issues that make 'em a little finicky. With proper maintenance and the willingness to deal with them, yes they can go quite a long time.
If, however, it was a $3k project to get the boat running right and a $5k price to replace it with something more modern - my opinion would be to spend the extra $2k on the replacement. If you're really hung on the Grew, and don't mind the garage time you'll have to spend on the boat - it may not be too bad to deal with.
I actually like my boat quite a bit, and actually like the Electric Shift Stringer for a few reasons over the Mercruisers I've run. But I don't recommend the drive system if you can get away from it.