The Vertical Software Trap
Some time ago I helped a person move to Linux. Primarily he uses Firefox and Thunderbird. He probably would consider Hara-Kiri before using a terminal for anything. He is not a computer person.
At the time I helped him migrate to Linux I was unaware about his bookkeeping needs. He has a small family farm business. I have since learned to be more thorough in my assessments when helping people move to Linux.
As he is not a computer person he did not provide me this information at the time we discussed migrating to Linux. His sole motivation for moving to Linux was the end of life of XP.
As time rolled along I learned more about his specific needs. I informed him that Quicken does not run on Linux. That he could migrate Quicken 2008 to GnuCash.
Later I discovered he buys a new version of tax preparation software each year rather than pay an accountant. I informed him that there are no tax prep software packages for Linux. The best he could hope was running the tax prep software in WINE or a Windows VM.
This is a strict point-and-click person. I do not try to convert such people into something they are not.
In hindsight, had I known his bookkeeping needs I would have recommended he stay with some version of Windows. Since migrating to Linux his bookkeeping needs have been a proverbial thorn in my side.
As much as I admire the engineering skills of the WINE developers, WINE still very much remains a game of fitting a size 10 foot into a size 9 shoe and hoping no pebbles get into the shoe. As this person is not a computer person, I cannot recommend WINE to such users with any degree of confidence. Especially after reviewing the WINE database and surfing the web for related experiences.
WINE wrappers such as CrossOver and PlayOnLinux do not change the fundamental equations.
While there are plenty of articles online about migrating from Quicken to GnuCash, he has resisted migrating to GnuCash for the same basic reason as most people. He has his comfort zone. He is not willing or enthused about migrating specific apps. Migrating to Linux has been stressful for him — and me, despite my repeated explanations that he is doing the same things he did in XP just with different app names.
While Quicken 2008 seems to be rated well enough for running in WINE, that approach does not resolve his desire to run tax prep software in Linux. Of which, I find no favorable reviews anywhere on the web or the WINE database.
He still dual boots XP once a year to run Quicken 2008. I long ago disabled the network connection in XP so he does not have to worry about fly-by malware. Sadly, none of the tax prep packages support XP.
Thus he now wants to run Windows 7. He is not keen on Windows 10 with all of the related privacy and telemetry issues.
He has made clear that he will run Windows 7 one way or another to run Quicken and whatever tax prep software he buys each year. He is not enthused that buying a Windows 7 license grants him only four years until end of life, but he prefers that to his concerns about Windows 10.
I explained to him that his hardware easily supports running Windows 7 in a virtual machine. He has a dual core CPU with virtualization extensions and 4 GB of RAM.
The option to install Windows 7 into a VM requires time. As does installing Quicken and tax prep software. As does importing the older Quicken data. Time that this person has to pay for. Even if he was willing to migrate to GnuCash on Linux I cannot resolve his need to run tax prep software.
And no, I am not willing to listen to geek poop work-arounds. The computer is a tool for this person. Nothing more. He is a person who uses the computer about an hour a day at most. His bookkeeping needs are annual and not daily. So the geeks in the crowd can simply take a long walk on a short pier.
This is a common challenge. While many people can migrate to Linux, comfort zones with vertical software prevents this. There is no way to avoid this problem. The only solutions are WINE and virtualization. WINE is unacceptable for non technical users. Virtualization requires competent hardware.
There was a time, a decade or so ago, when migrating from Microsoft Outlook was the primary challenge for migrating to a Linux based system. That challenge has faded. Today the requirement to run Quicken, QuickBooks, and Tax software remains an insurmountable challenge to migration. Especially for non technical users.