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.
Ultimately, when it comes to business, one of the biggest reasons to spend money is to buy yourself time. You probably could build an entire product yourself, but if you hired a few developers at $100K/year, you could build the product way faster. If you had new systems at $3K each (instead of buying used laptops from five years ago for $99 each), development would speed up. If you spent $2K/year on a third-party software suite, you wouldn't need to build it yourself or mess around with something not quite so polished. The flip side is that if spending money on something doesn't get you any benefit then of course you shouldn't do it.
Some people see benefits, and some don't. But making comparisons to narcotics comes across as quite childish.
Cost of Visual Studio Pro + MSDN for my (small) business was £1100. This for 2 years of MSDN, and it was some deal (at the reseller's suggestion) that also came with various Windows licences too. (More Windows 7 than I imagined was likely for the price, and I think Windows XP and Windows Server 2008 R2 too.) Renewal cost is something like £900.
I wouldn't refuse something cheaper, but the price seemed fair enough as these things go. For a side project this is perhaps a little steep, and if you could realistically use something cheaper you would be silly not to, but for a business with an actual need for all this Microsoft junk this seems like reasonable value.
Stuff that costs me less than £~500/yr: printer paper.
Stuff that costs me more than £~500/yr: everything else.
Then again, just to back up your point - my last employer switched everybody from MS Office to OpenOffice to avoid the licensing fees, even though numerous internal tools (that then had to be rewritten, at a cost of several man-weeks, plus drag due to changes in workflow for the less technical staff that used them) relied on VBA, COM and OLE stuff that OpenOffice didn't support. And the place I'm currently working with doesn't install Visual Studio on the servers (each server = 6-core Core i7 with 32GB RAM, 2TB RAID1, 1TB SSD) because apparently it would be too costly to do that. So maybe once you become big enough for MS to care about things start to become rather more expensive.
I tried making the software cost for my side projects $0, and the non-Microsoft community does make it feasible, but I'm way too invested in Microsoft tools, so the productivity hit was way too steep.
I started with a stack of Grails + PostgreSQL, hosted on AWS (Elastic Beanstalk, etc.), it worked pretty nicely (I was particularly impressed with the ease of use of Elastic Beanstalk for an absolute newbie).
What I need is some free time, or a job switch (working on the 2nd part :) ).
Still, I tried most IDEs and other ways of development (Eclipse, IntelliJ, Sublime Text), and I still like Visual Studio the most. I also like Microsoft SQL Server a lot.
The Microsoft stack is certainly a lot more expensive than an equivalent stack if you have to pay for it, but having the BizSpark option, it makes a lot of sense if you come from a Microsoft background.
I've never been in the situation to make these kinds of decisions, but when you're paying tens of thousands a year per developer, sysadmin, qa, and/or ops people, a couple thousands per in software costs isn't going to break the bank.
I strongly dislike those books. I think LPTHW is perhaps good if you already know programming. Otherwise, he's just trying to get you stuck. Not what you need when you're already barely hanging on.
I also HATE how arrogant he is on the web. I dislike him as a person and thus can't bother with his classes.
I'm sorry you strongly dislike those books. I think they're quite good. I can't imagine why you would say he is "trying to get you stuck". Do you have a specific example?
I have taught zero-experience, low-aptitude beginners for nearly two decades, and his approach is basically exactly what I do with my own students.
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.