I see a problem with this approach. In 5 years much of your equipment will be obsolete and have almost zero value on the second hand market. And if you do decide to use them, everyone will have moved on to new media/software.
Technology only becomes obsolete when it no longer solves a problem you have. It becomes irrelevant when it solves a problem you no longer have.
He is investing in stuff that will allow him to create. The only problem is if he can't create stuff faster than his competitors (not much of a problem if you have enough talent and skill) or if people suddenly become no longer interested in the stuff that he wants to make (which also seems unlikely).
I don't see anyone creating anything with an 8-track or VHS tape except as a novelty because it would be painfully slow and the quality not up to par compared with what we have now. It's only useful if he's creating stuff and earning money/fame/fulfillment or whatever rocks his boat. But as 'investment' for some future date when he decides to use them he might be better off investing the money pending that future date which brings us back to square one.
He is investing in stuff that will allow him to create. The only problem is if he can't create stuff faster than his competitors (not much of a problem if you have enough talent and skill) or if people suddenly become no longer interested in the stuff that he wants to make (which also seems unlikely).