Matt -
Don't put yourself in jeopardy.
Do a "fully bootable cloned backup" first of your current setup using either CarbonCopyCloner or SuperDuper.
Also, I recommend that you download the HighSierra installer but DON'T run it (just quit when prompted if you wish to install).
Use a USB flashdrive (16gb or larger) to create a bootable USB installer, and boot and install that way.
For creating the flashdrive, I suggest ONE of the following: "Boot Buddy", "DiskMaker X", or "Install Disk Creator".
Probably a good idea to make A SECOND COPY of the installer somewhere else for safekeeping before you create the flash drive installer (saves having to download it again).