Dear @Xtract ,
Switching from an other OS always requires A LOT to learn.
Previously you wrote above what I filtered so, you are still in discovery and decision really :
→ Why macOS ?
→ Why Linux ?
→ Why Haiku ?
So you had not decided, and you would like a (rich) list of applications
that worked on Windows – and … works here as well
The questions about Wine also implicates this -
you indeed want to avoid the learning curves - if possible - that needs to be walk through as even the familar programs on ANY OSes ABOVE will be available …
I must share the sorrow truth : the OS itself - and how it is working -will be different. Always.
So they won’t work as a little bit other Windows. I tell it as you wrote you are not an IT expert.
I can assure you :
anyone can learn macOS , Linux, Haiku
if accepts that … it will be new for them, and they have to learn A LOT.
The OS, and the new programs those available for them for a task they want to execute.
I say so as I can take myself an IT expert - on a scale 
– as I had worked as IT admin on several UNIXes, Linuxes and also in work and at home used Windows (from 3.1 to Win7) and Linux (different distros) for longer years …
… and now Haiku for longer a year
and almost a year as daily driver.
For me also : Haiku is a learning curve.
As from last questions we can see …
you wouldn’t finally terminate the usage of Windows - even you would asked how Haiku is a daily driver - also mentioning your question regards Haiku as a work environment.
Then your decision is to switch to an another OS than Windows is easy.
I accept your decision you would use longer as many familiar programs as you can to your working environment.
Select the next OS depending on
which offers the most familiar programs – natively !..
This way you would not need to learn how to /use/configure Wine or face to that : that program cannot be used with Wine (such things can happen! ).
Such “talk” should be scpecified …
Anyway, if you interested in … Haiku knows the Win workgroup domain. You can add your existing workgroup on Network config panel and install Samba which is the open source solution to that (File and printer services) protocol, so file transfer among them can be secured this way.
However, how to configure you must learn. The Other OSes also use Samba, so to learn it - useful … in case any other OS you would select finally.
From your question I understand you had not used LIVE CD / USB earlier
not even Linux or Haiku.
Live CD / USB is still an installer material - just a special one.
The simple installer materialcontains :
→ bootloader (BIOS and/or UEFI one : Haiku since Beta4 surely offers both)
that will boot into installer
→ installer software
→ the OS and the bundled apps with it - in a kind of installing packages.
And also there so called network install, in this case a minimal config exists that enables that installed OS components and apps selected downloaded and installed from (a) network destination(s) - so called repositories (or repo, as they called aslo ) .
Of course there is a hidden, small OS under the installer that is booted to have the installer software running, but that is not available in case a simple installer.
In case Windows installer - the Windows 7 installer media was the first that enables to have a reduced OS - other than the installer, but this is rather for recovery purposes. Anyway - back on track …
… So Live CD / USB differs in that - it contains
→ bootloader (BIOS and/or UEFI one : Haiku since Beta4 surely offers both)
→ installer software (in case Haiku it is within the OS image)
→ the OS and the bundled apps with it - in a read-only image file
On a Live installer you can boot into the Installer or onto the Live OS, that will be booted from the image.
So the full OS is available in an “image” (basucally read-only due to the CD/DVD itself) format on the install material.
The image means that in a same way as it is would in installed form on the final destination … e.g. in the hard disk in your computer.
So not installable, but executable way … this way you can try out.
The Live CD/DVD/USB can use up this - you can select the Live version when the installer boots.
In this case not the installer starts BUT the OS itself from this image file.
I said this image is read-only - if it is on a CD / DVD as they are read only in itself - the ISO CD ROM format basically not writable - at least not the OS images as they are not written to an optical disc that way – but in a ISO ‘CD-ROM’ not in packet writable CD session or DVD RAM that requires special optical drive. (Thanks to God and engineers – it would be reeaaalllly slooooow ! )
It can be different
in case USB thumb drive - in that case the USB contains the image such way that is writable (or not, I will describe it later).
So if you install something from a Live CD/DVD’s running OS
it will be installed into your RAM onto a ramdisk :
it will be in the RAM until you shutdown or reboot the machine.
As I used Haiku mostly from Live USB not CD/DVD when I tried to install packages, I am not certain as in case Haiku itself. As Haiku is on a BFS on CD/DVD and do not assume devs prepared a different way
you may get error massage to unsble to install as it would try to install into the BFS image on the CD/DVD - that not possible.
So without certain - I think Haiku does not use a ramdisk for this as Linux distros does where no persistent storage present (at most ones).
One exception that can harm your installed Windows - if you do something with your hard disk using the available commands programs in the running Live Haiku.
For example
you start the Haiku Installer
and then
there is a part when you have to prepare install place for the Haiku install – even on your hard drive - if no other drive available.
Of course
you can select an USB thumb drive
- or external drive or other drive in the machine you have -
to create and install there
or not install anywhere as you have a Haiku already in the a Live format.
SO in case CD/DVD
primarily hard to damage your installed Windows, but possible.
Ok , so in case USB, and many Linux distros the same as in case CD/DVD installer as often there is no so called ‘persistent storage’ prepared. The installer and the CD image resides on a FAT32 partition - so you must create manually a filesystem and mount it - otherwise the Linux install will be doing into a ramdisk.
Not in case Haiku Live USB - in case Haiku image resides on a valid BFS (Be Filesystem) partition - this way if you try out to install something the installation will be happen here (on the USB drive and until the available free space on it).
But you must consider the Live image partiton is small, especially in case Haiku 64bit - to avoid huge download size when get it in ISO file :
Beta4 DVD : 1.4 GB
Nightly CD : 700 MB
So if you want install Wine here then the Haiku package manager might want update the OS as well and you won’t fit here, as for safety purposes Haiku
saves the old packages that those update,
download the new packages
and Wine as well
Finally then you would put here the Windows software to install.
So in case experiment with Wine from a Live Haiku - we are there what others suggested
install Haiku in a test place - at least with 14 - 20 GB to have enough free space. Haiku won’t occupy large space like Windows
Welcome to the Haiku shell.
~> df -h
Mount Type Total Free Flags Device
----------------- --------- --------- --------- ------- ------------------------
/boot bfs 14.0 GiB 9.9 GiB QAM-P-W /dev/disk/usb/0/0/0
/boot/system packagefs 4.0 KiB 4.0 KiB QAM-P--
/boot/home/config packagefs 4.0 KiB 4.0 KiB QAM-P--
/boot/system/var/shared_memory
ramfs 0 29.6 GiB QAM-PRW
Thisd is my install now - Haiku 64bit R1B4 base install (first line : /boot ) no updates available installed until now.
This is ten times bigger than Live Haiku ISO image.
As you can see almost 10GB is still free. However I had not unselect packages from base install - so a base developer environment and the usual demo progs also installed.
I installed 2 command line progs 2 packages to have themes installed and StreamRadio, as those have not dependencies or had not pulled the whole update to latest as others I issued and finally cancelled.
So, the decision on you.
You may continue your discovery –
look at the same things at
macOS (that requires new HW as well) ,
GNU/Linux distros (many-many selections to decide :
which distro ?
which graphical server : standard X11 or Wayland ?
which window manager ?
which graphical environment : Gnome, KDE, XFCE, etc ?
Without intention and dedication moreover hard will to learn NEW and A LOT - you may stay at Windows.
