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The reliability of a 240 with a couple of decades and tons of miles on it is *very* heavily dependent on the sort of care it received in it's prior life.
I have a 1993 wagon that was pampered for 119K miles in NYC before I got it. A massive pile of dealership receipts for all the scheduled maintenance, and some hypochondriac repairs as well (it made a noise... REPLACE EVERYTHING!). In any case, my wagon is a real peach. Other than me doing un-advised science experiments with the motor and blowing it up occasionally (300 HP at the wheels has its price, coming and going), my wagon is a peach (145K miles on it now).
Bought my daughter a 1991 244, with 150K on it. It's been problem after problem. Some minor, some not. It's had a recurring issue with it setting various codes and getting 18 mpg. The radiator leaked trans fluid into the coolant and vice versa. The tailshaft bushing on the automatic went out. The wipers went from working weirdly to not working at all. Of course, the taillights are incredibly erratic (sedan printed circuit taillights = *tearing your hair out*). Had leaking exhaust manifold gaskets, no sooner had I taken that off and replaced it that it started tossing out 'Headgasket' symptoms. She left it in town while she went off to college for a semester. Problem after problem. There was a stck of receipts from the previous owner as well, but for all sorts of weird repairs that some shady shop overcharged for (and many of which were still not right).
In any case, I think the idea is that some cars have built up a massive maintenance deficit from previous owners. The car may still look nice, but it will likely be a money pit for some time. Of course, at some point you'll run out of things to keep fixing.
And a Miata? I have to say, I can't blame him. In February of 1990, I traded in my BMW 318is and got a red package B Miata. Enjoyed the *HELL* out of that car for the next 6 years of my life. I'm not sure how many things Mazda gets right as a company, most of their cars are FWD lumps of which I have no interest at all. The RX8 is a rotary powered car still, eats gas, makes no torque, interesting to some but not me. Don't care about most of their CUV crossovers either.
But the Miata is one thing they got incredibly right. It's a Lotus Elan, with 500 (600?) lbs of reliability and durability added (1550 lbs vs. 2100?). It's incredibly fun. If you don't have a stopwatch or notice minivans pulling away from you at lights it feels fast. It's an incredible joy to drive on twisty country roads. It's one of the few cars I was ever compelled to frequently drive around for no reason other than it was so fun. Top down in the winter (heater blasting), top down in the summer (A/C blasting). All the charm and enjoyment of a Brit roadster, all the reliability and durability of the best Japanese cars. To this day I still occasionally troll Craigslist looking for cheap 1st gen Miatas, only thing holding me back is I'd need to get rid of one of my Volvo's, and I can't bring myself to do that.
So really, can't fault either choice really. Obviously, the 240 is a more practical car, the Miata has two seats only, barely any room on the shelf behind the seats (if the top is up), and the trunk is tiny as well. But other than that, the Miata is probably as durable as the 240 is (people put 250K on them routinely, driven hard the whole time), and probably a fair bit more reliable as well.
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'63 PV544 rat rod, '93 Classic #1141 245 (now w/16V turbo)
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