I think he'd overcome that. One must remember that to many horror critics his main fault was a tendency to turn his monsters into scientific phenomena. There is also the fascination he had with academia and books. With the possibility of putting vonJunzt's "ForbiddenKulten" on Gutenberg it is unlikely that Arkham University could ignore the Internet for long.
Not to take the thread off-topic too long, but....
On the last point, I certainly agree. Joss Wheedon has remarked that this is one of his biggest mistakes concerning Giles: his resistance to computers and the internet -- a definite drawback for a librarian.
On the other points... While Lovecraft looked askance at most machinery, he did enjoy his one airplane ride -- but noted that such things were "okay" for a jaunt, but he hated what they likely portended. He also enjoyed a speedy ride in an automobile, but felt much the same there. And what it comes down to is not only his mechanical ineptitude, but his intense belief that composing anything on such did not allow for the other aspects which contributed to doing one's best work. I not only refer to the speed of composition (for, as Tolkien called them, "the ten-fingered"), but the aesthetics of the words on actual paper, and the ability to go in and alter, transpose, scratch out, etc., an almost infinite number of times... while still having all the various choices there visually. Lovecraft was intensely sensitive to such things and, while the computer allows for a fair amount of that, I don't think it comes anywhere near allowing what one sees with a page of HPL's original holographic manuscripts... which, for anyone except HPL, are a grand royal pain-in-the-neck to decipher a fair amount of the time....
Also, he apparently derived a certain psychological/emotional pleasure from the action of scribbling with a pen (or, when his nerves were particularly troubled, with a pencil), and that is something, again, which the computer simply does not allow for.
So, while it is possible someone might have been able to get him past these blocks and actually using this nifty little tool, from all my knowledge of the man, it is about as likely as "Tricky Dick" Nixon admitting he was a crook.....
As for his turning his "monsters" into phenomena... well, essentially, that is what they were: symbolizations of the mechanistic, uncaring, and often completely alien universe. They tended not to be characters, but rather phenomena given a form of life....