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If you look at Jay's website, http://www.jaylenosgarage.com/ you will soon see that he employs a fair-sized staff who maintain the cars, rebuild new acquisitions, and work on a number of projects around the garage. With all this, Jay is an amazingly knowledgeable expert on old cars and their maintenance - and he spends practically all of his off hours turning wrenches himself.
Not only does he work on them, he drives most of them regularly.
Jay was also a car guy and full-time mechanic long before he made it big in show-business. For him, at least, the collection seems to be more a realization of boyhood dreams than just being able to show off his wealth.