Here's a suggestion I haven't seen:
Unless you have full management support, a skilled team, valid business reasons for this conversion, and expectations of succeeding, consider moving to another company/job.
You've been given the task of digital archeology/septic cleanup. Unless you like the tedium and stank, it's not going to bode well...
There's a lot of open data available, depending on what you are looking for. If I had time, I could probably spend it on this SE and earn points, count coup, or whatever. Instead I'm working with a couple of user groups helping local programmers analysts learn how to dig into it. We have a few specific data sets that we use for different types of analysis, demographic, mapping and financial.
On the other hand you do have companies that do make millions that are bailing on certain aspects of Microsoft tools and servers due licensing costs and increases. I've been involved in IT budgeting for almost two decades and the CFOs don't always sign the check just because it's an IBM/Microsoft/Oracle solution.
The OP has "dabbled", he hasn't committed himself to a single language nor a good regimen/project to succeed. Let's look at this quote:
"On top of that, there’s a constant din of “Python’s not for you, it’s for them ({scientists, academics, hackers, statisticians, someone else})” out there if you look up stuff about Python."
Really? Sounds like a bad excuse to me. There's a fuck-ton of tutorials and books for Python beginners of all ages and backgrounds. It's one of the few languages I recommend to newbies for that reason, beside the fact it's easy to be productive in. We have a full spectrum of users at local meetups and I chat with the scientist and tutor the beginners. Python users are diverse as a crowd at a state fair.
And coding isn't programming. There's a lot more to know than the syntax of a few languages and APIs. It's a whole universe to explore and learn how to control and leverage. You can find a cool project, then drop down the rabbit hole the rest of your life, enjoying the beauty...
Having been "online" since the '80s, I respectfully disagree. Relative anonymity in "real" life leads to antisocial activity and rudeness since there's little chance of identity or recourse. Consider the behavior of automobile drivers.
Anonymity online can't fully be achieved except by a small few, but the positive benefits can be simulated for many by careful operators of BBS or internet forums.
This is similar to what I would do in the same situation. If I didn't need the income of my day job, I'd spend the time on public service or charity of some sort. I can't see myself spending money like a trust fund dilettante nor funding yet another startup.
It's not debugging as much as what us old timers call troubleshooting. At the university I had an insane advantage over those folks that had never seen a Simpson multimeter nor soldered a component nor seen a schematic. I had spent my teenage years building radios and computers followed by formal training in the military. And the Navy taught us how to troubleshoot large systems down to the component level. So college was mostly easy and extra beer money was earned fixing other students electronic devices and tutoring.
I refused to install Skype for work, pointing out that it's not as secure as it's alternatives. Plus the fact it's disrupting, crappy software and you still can reach me by email, phone, VPN or walk down the hall to my office.
I agree with the author in regards to coding web sites. It's not enough to know a just a few languages, there's a whole frickin' vocabulary of crap piled on layers of services and frameworks frosted by the JS flavor of the week.
Or just configuration. Everybody wants to reinvent Make and they all do it wrong...
While I love the blog and the very clear explanations, none of this is new nor amazing to the experienced RF engineer, enthusiast, or practitioner. What's awesome is that the hardware and software are currently cheap enough that more people can discover and enjoy the larger spectrum around them. Welcome!
I chose my laptop mainly on the quality and layout of the keyboard. Unlike the OP, I don't travel as much so I had more choices due to the fact I have 17.3" laptop.