Paint Tool Sai on Mac with tablet pressure

How to: Get Paint Tool Sai running on a Mac with tablet pen pressure support

Surprisingly a lot of people don't know that you can do this.

In every stream someone asks, "What program is that?"
Artist replies, "Paint Tool Sai"
Then someone else says, "I want Sai but I can't use it because I have a Mac,"

Not true!  You actually can.  It's not that difficult, either.
Using virtualization software, you can get Sai running on a Mac inside a window as if it were a native Mac program.
I use it to ink almost all of my pictures, in fact.

Fair warning: This does cost a bit of money. You're looking at at about $150 at minimum to buy both Sai and Windows licenses, and add another $79 if you choose to get priced virtualization software.
At that point you might want to consider instead getting Photoshop Elements 11 for Mac ($100), but if you want to run Windows software and games on your Mac as well as Sai, this would be the best option.

This video demonstrates what it looks like:



ESSENTIALLY what you'll be doing is installing a Windows "virtual computer" inside your Mac, and Sai runs in this simulated environment.
In other words, Sai has no idea that it's running on a Mac; it thinks it's running on a typical Windows PC.

To get this working, you'll need the following:
1. Windows license (I recommend the 64-bit "System Builder" or "OEM" version for $99 from Amazon or Newegg)
2. A USB flash drive that is 8GB or bigger.  Download the Windows 10 ISO you'll use this later to create a USB flash drive installer and use the product key included with your copy to activate it.
3. A virtualization program. Your choices are: VMWare Fusion - ($79), Parallels Desktop - ($79) or Oracle VirtualBox (free). (I personally use and recommend Fusion)
4. Paint Tool Sai - Buy a license and download it at Systemax (they take Paypal)
* Sai costs about 5250 yen, or about $50 USD as of this writing but this will change depending on international currency exchange rates.
* ONLY get Sai directly from the official Systemax website.  Unofficial or "fan-made" versions are often bundled with malware/spyware (especially the pirated versions... don't bother, it's not worth the trouble)
* Save your Sai license email confirmation that contains the license codes and store it somewhere safe where you can find it later if you need it - (e.g. to reinstall it) - Do not lose this email!

Procedure:
1. Install Windows on your Mac using the Boot Camp Assistant program, which is located in the Applications/Utilities folder on your Mac's hard drive.  Carefully choose how much hard drive space your Windows partition will get; if you change your mind later you'll have to erase the entire Windows partition and reinstall it all over again!  I recommend setting aside 40 GB at least - you might want more if you plan on installing games, but don't give it so much that your Mac OS X partition has no space left.
2. Switch back to Mac OS X (hold the Option key as the computer starts up to pick Mac or Windows) and install one of the virtualization programs mentioned above
3. Launch the virtualization program and tell it to use your Boot Camp partition to create a new virtual machine (it will probably ask if you want to do this the first time you launch it).  It will guide you through the process.  Note you might be prompted to re-activate Windows in the virtual environment; do so using the phone-based activation method.
4. Connect your tablet to the Windows virtual machine (look in the virtualization program's USB options menu).  Note it will no longer function in Mac OS X until you disconnect it from Windows - this is normal behavior.
5. Download the tablet drivers from the manufacturer's website and install them inside your Windows environment (having the drivers already installed in Mac OS X is not enough - Windows needs them too).
6. Download and install Paint Tool Sai in your Windows environment.
7. Enjoy using Sai on your Mac, with pen pressure support!

Remember that you always need to connect your tablet to Windows to get it working 100% with Sai.  To make things easier, dig through your virtualization program's settings to enable the automatic connect option for your tablet.

* Note: You can actually skip the virtualization program and just use Boot Camp mode to run Sai. The only problem with this is that while your Mac is in Boot Camp mode, it's 100% Windows; you won't be able to run your Mac programs alongside Sai this way, and all files on the Mac partition of the hard drive will be read-only (basically, while in Boot Camp mode your computer becomes an Apple-branded Windows PC). Boot Camp mode is GREAT for playing PC games (it runs them as well as a similarly specced PC would) but if you want to use Sai alongside your Mac programs, you'll need to use a virtual machine. More info on Boot Camp mode is here.

Any questions, I will be glad to answer.