C is not the path of least resistance for the OP. He is neither trying to make a career out of software engineering nor hack on a UNIX kernel.
He wants to be at the fringe of business and software and these days if that's where you want to be you can "get by" knowing only a high-level language really well and hiring/partnering with more specialized engineering talent as needed if the business-side requires it.
Mastering the high-level language is arguably as difficult as mastering C but the leverage you get from the high-level language is huge relative to C for the sort of business/software problems that will be of interest to him.
Yes, I am in complete agreement with you. Which is why I suggested C.
You only realise the huge productivity jump when you first program a small application in C and then do the same thing in Python / <your favourite language here>.
It's still a waste of time. There will be enough problems to learn from, no matter what he chooses to build. No need to introduce artificial problems.
I think one of the ways to spoil one's career is to litter one's life with artificial problems that one deems necessary for success. I feel reminded of the Japanese criticism of the MacBook Air recently.
I would argue that any developer should spend a couple of years maintaining a small to medium-sized application written in C. It's like eating bran: not a particularly huge amount of fun, but good for you in the long run.
We can't possibly be in complete agreement if we are drawing opposite conclusions.
I think the difference might be that I assume the OP is heavily concerned with efficiency.
Given his background and goals it is not efficient [1] for the OP to learn C when in the same amount of time he could learn a high level language and then directly accomplish his goals, and never need to learn another language for the rest of his life.
[1] achieving maximum productivity with minimum wasted effort or expense (O.A.D.)
My personal experience has been that I am much more productive when programming in python. More gets done easily, and the code is very readable.
However, I realised this only after I had spent order of magnitude more time on doing the same thing in C, and burnt myself plenty of times during the process. My point is that you find out how productive you can be in one language when you have used another language to do the same thing - then a comparison becomes somewhat meaningful. I had read a lot about how python makes you more productive, but I experienced it only when I started coding in python to achieve tasks that I used to code in C earlier.
The same goes for shell scripts that make my life easier. Shell scripting became a hellish experience when I was using a solaris machine for some time - but by writing a python script instead of a shell script, I could be pretty sure that it would run in linux / solaris / any other *nix.
So, I still believe that we are essentially in agreement regarding productivity. Efficiency is another matter though - inspite of psyco etc, python tends to be slower in some tasks and it might be well worth the time to code them in C.
I think we're speaking different languages (despite the fact that it appears we're both speaking English). :)
I know you can reduce development time using a high level language to solve problems like this. So do you. And now so does he because we told him. No need to have him waste time proving it for himself.
And to be 100% clear when I said "efficient" I mean efficient as relative to life/goal achievement. I did not mean efficient as relative to CPU time or memory usage. One of my assumptions is that if this guy implements something successful in Python he'll be able to hire or partner with someone who has a real engineering background and can make "it" go fast using every trick in the book.
if you do not like C programming,
"How to Think Like a Computer Scientist: Learning with Python" to learn python.
available for free on the net