The switch to a Linux based operating system is not as complicated and daunting as one may think. Over the years this process has been streamlined. The amount of technical knowledge that you need to have has also been lessened by critical pieces of automation during install.
A good comparison would be Arch Linux vs. Ubuntu. The difference in these installs is night and day. Where Arch won't do anything that you don't specifically tell it to do. Ubuntu will do what it feels is the best, allowing you to change these setting and choices later if you feel that another approach would be better.
This is optimally what you want if you are going to be doing the setup yourself. When you seek out someone to install and administer your system, you will likely be exposed to a user that has their own biases.
You really need to make your own choices and see what companies are offering and define what your going to be using your machine for.
There may be software that is critical to your life that is not available on Linux, so this is something that you need to think about from the very beginning.
To me, this is not a deal breaker. Though it maybe a bit of a time suck for a few days. If you have a professional that you are working with, or you are confident asking questions in forums, you will likely be able to fix or circumvent issues related to incompatibility and proprietary lock-out far easier than an initial review may infer.
Just like building a custom car, you should know what you are getting into and how to navigate the possible challenges you will face. Though it is impossible to prepare for everything, with DaaS you should be able to compensate for anything that you may run into, in the worst case.
For the most part you will find a bit of a different methodology, though many things will seem familiar, especially if you are using one of the more commercial distros, or an actual commercial offering from XFCE, Canonical, Redhat, or similar.
The thing that you will really want to concentrate on is hardware. Take the time to go through what you have that is compatible, and sell what you can that isn't -- if that is an option. If not, again, DaaS or a VB solution will give you the ability to use what you need and still be able to comfortably make the switch. This is assuming that you have the required hardware to support such extravagance.
Though you don't need a lot of what is out there. I would suggest to do things through web applications and, so-called, Cloud-apps. This saves a large amount of time and cost. Things that we can always use more of.
Finally, I suggest that you get a notebook. Yes, a notebook. One of those ancient tablets, made from dead trees, that allows you to store information that you manually write into the system. Keep it in a safe place particularly locked and fireproof if possible.
Write down everything that you do and change. Now I am not talking about each file that you more, but major changes, like installing software, drivers, and kernel changes. This can be invaluable if you ever have real system problems. This could also be something that you just log in the system and then print each day, or before you log out, when you make a backup, etc.
Linux is not hard, and usually doesn't suck. Though sometimes you may find that one of your favorite vendors, or those more coveted, don't support it. The only way to change this is show them that there is a market for their product in the Linux world.
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