Brotherhood wrote:
Instead he wants to slog out the seemingly most difficult path that has. Big chance of not working out
You are wrong.
If he's a halfway good bartender, he'll be amazing dealing with customers. I know from personal experience. If he treats the customer like he's behind the bar it will be fine.
As someone that's in the industry, there are so many tech geeks who openly complain about "the customer" (could be a project manager, could be a paying customer) it's not funny. They have zero clue how to interact with people and want to return to typing. In one way, it's fine. They could be very productive coders. In another, it's very difficult to get the customer's needs met.
Your brother can cross that divide if he plays his cards right.
And coding at this point isn't that hard. As long as he sticks to C or python or perl, he'll be fine. If he works on dying languages like java or fortran, he could have a nice niche over time. If he's got an interest in assembly, it's probably a bad idea at his age. As long as he sticks to the common, higher level languages, he'll be fine.