Just a perspective from a not yet TR owner (still lurking)... I think I think the 'cost of ownership' to be a very interesting statement, at least to someone who does not yet own one. Nobody here would question the TR's image, collectors appeal, and just all out 'fun to drive' ability. However I have observed that there really isn't a 'good' find out there where you are not taking a leap of faith which no matter where you land falls into a money pit.
If I happen to get a TR with 10k legitimate miles, garage kept, babied etc, I can still count on the brakes failing (best advice is the vacuum system replacement), the paint or bumper fillers going bad, and the seal or welding going bad somewhere near the head covers. (correct me if that is inaccurate hehe). So if I buy one before those fixes were made, I have to incur those costs. Or if I buy one that already had those repairs done, I have to contend with the 'pot being stirred' of other potential issues that were caused by the execution of those repairs.
I have an idea in my head (not based of any fact whatsoever) that if you bought a car from the 60's you got one 'back when they KNEW how to build them' and if you got it working, it would work for good. And if you bought one from the late 90's on you got one they built from the 'computer fitted parts', long warranties and the rise of the 'factory recall' and there was always someone you could yell at to help get your car fixed. But the late 70's through late 80's seem to be the 'experimental' age for car manufacturers. Lots of 'Let's try this and see if it works'. and i think the TR is an excellent example of that. Not to mention that we all know the leap of faith leads to a money pit no matter where you land, but we still chose (or will choose) to jump.
IMO these cars are indeed toy cars, that need to be treated just like a woman. Sure they will give you the ride of your life, but if you dont spend enough month on them each season, they will take you for half your income later on. hehe.