If your image checked out and you get the black screen after install press Ctrl + C and you'll enter a burgundy screen which will boot to the OS. You won't need to Ctrl + C all the time, just when you get that blank black screen the one time.
I don't believe you can run wine on Linux live disk to run an old windows game, you need to have Linux installed to get wine services running to do what you attempting.
all you have to pay attention when making a USB Linux or Other OS Thumb drive bootable device, is how old is your PC is, if you use RUFUS (which is what I use) you can define the format of the partition to be MBR UEFI or MBR Bios/UEFi for compatibility with older computers
Ubuntu uses about 4.5 GB of space installed. so if you boot from one, and install it on another thumb drive make sure it is at least 8GB I would suggest 16-32GB considering 3rd party drivers, files space to download, and install wine/game then you should be able to boot on that final install thumb drive.
it will not be performant by any means as the thumb drive is 2.0 or 3.0 transfer rates. I prefer to use an old laptop drive in an external enclosure, and basically did what you are trying to do. and when I want Linux to run I plug it in reboot machine
and do what I need to do 500Gb is a nice size