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Three things you have to worry about:
Maintenance
Spares availability
The Achilles heel
Maintenance isn't that big a deal, really. In the older cars, there's more of it compared to something like a Porsche. The big ticket items are valve adjustments and cam belt changes, for those engines that require them. If you do it at a dealer, it will be expensive. Independents can sometimes do it cheaper, a there are less time-intensive ways to do some things. It can be done by an experienced individual but you won't enjoy it. Cam belts can go longer than the 3-5 years people suggest. 7-9 is doable, or inspect them periodically and replace them when they show signs of age. Older chassis needed more suspension maintenance than a Porsche. Bushings and whatnot. Ferraris will do high mileage but you'll replace things that were thought of as "lifetime" in a Porsche. No idea about the newest stuff, maybe it's better in this respect.
Some spare parts are now just wishful thinking for some models. That would keep me out of anything older than the 1990's. Haven't been a Ferrari owner for a few years now, it could now be worse. Prices for some things are stupid. Not necessarily routine consumables, but things you might break once in a while. If you can even find them...
The Achilles's heel... Many of these had issues that were stupid expensive to fix (if you could even fix them and keep them fixed.) Take the 355. Depending on which one you bought, you might have bad valve guides (40, count 'em) or bad exhaust manifolds, or an irritating problem with a "sticky" throttle. If you bought a 412, you get to experience their window lifter issue. Many models had the soft tough interior trim paint that went to **** after a decade. Etc.
I'm no longer part of the Ferrari world for a bunch of different reasons and have sold off my cars and all my other Ferrari crap. So, I also don't follow the current market or pay attention to what's been rolling out of Maranello for the last 10 years. Might be a good one out there, might not. Don't know, don't care. Just do your homework and never by one that needs anything. You want one that needs nothing, because it will have been cared for by someone properly. The ones I've seen here recently from bring-a-trailer... you couldn't give them to me for free.
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