I’d say when there’s more than an hour’s drive between them it’s reasonable to expect people to tell them apart, even with similar names.
Even if they started at the same place, it would be the hiker's responsibility to verify where he is and that he was on the intended trail, not just at the start, but as he progressed along it. If what you are seeing around you does not match up with what your map shows, go back to the last place you were certain.
If this guy's life was in danger - and, having been to Taylor's cabin myself, I can well believe it was, especially given how clueless he was - then he has bought the rest of his life for $300K, by abusing an infrastructure set up with considerable effort by people who are doing their best - and taking a risk - to act responsibly. He should be grateful for that and quit whining.
Though I do feel bad for the people who live on such streets, with how often their food delivery gets sent to the wrong place. Turns out delivery drivers aren't always the ones with the greatest attention to detail.
"No."
"I didn't think so."
Also Vanbrugh Castle as a house name within the same radius but, obviously, isn't on any of the aforementioned roads.
And when I am going hiking on a route I had not been on before, I take a map of the trail and use it, especially at a time of the year when one should expect temperatures exceeding 35°C.
If he had made his way to his intended hiking location, it is quite possible he would still have become lost, as the trail system there has many branches.