I bought my 85 Carrera in 1995. I have not had a car payment in this millennium.
It is worth right about what I paid for it all those years ago. I have driven it 70,000 miles in 18 years so 3,800 miles a year. Not a ton but more than most owners of old 911s.
I have had immeasurable fun in the car. I have driven it to both coast and to the Upper Peninsula of Michigan. I have see deep triple digit speeds on the track at Charlotte Super-speedway, and the Rocky Mountain National Park. Over 20 National parks total. I have done over 100 autocrosses, several DEs and a lot of road trips.
I did not buy it as an investment. I really hope the prices of 1980s Carreras go up like the early long hoods. If they do great. If they don't that is OK. I will keep my sorted and very nice Carrera.