Kind of reading between the lines, this sounds like a guy with a lot of romance and nostalgia, but not a lot of mechanical savy. Bad combination if you want to daily drive such an old car. And he didn't exactly pick a good one, either.
My daily driver is my '70 Beetle. Way more modern, luxurious, and powerful than Thom's old beaters.
Yes, it can be done, if you are familiar enough with it and in tune with it. Hell, the newest car I have ever personally owned is my '72 911. The new stuff goes to the wife. Sounds like this guy needs to go back to the new stuff; he sounds a lot like my wife.