I realize this is a necro-thread, but I feel like I'm in a unique position to shed some light on the answer to this question.
I was on the installer QA team for "Unity", System 7.5.3 revision 2, and I was personally assigned the task of testing the installer on the Mac Plus. While the OP's question was related to System 7.5.5, the challenges with 7.5.5 are going to be at least as difficult as the challenges with 7.5.3r2, so I'll address the problem of installing 7.5.3r2, and those should translate to similar or identical issues with 7.5.5. (Disclaimer: I've never installed 7.5.5 on a Plus, that I can recall.)
Of all the Macs supported by 7.5.3r2, the Plus was particularly difficult to install it on, because of a requirement that the 7.5.3r2 installer be launched from a minimum of System 7.5. Someone indicated above that 7.5 requires 4 megs of RAM, and I have no reason to not believe that. In modern times, if you own a Mac Plus, there's no reason why you shouldn't have 4 megs of RAM in it, so that shouldn't be a problem. The problem with System 7.5, of course, is that a bootable System 7.5 install will not fit on an 800K floppy disk. So: To run the 7.5.3r2 installer, your Mac Plus cannot be booted from a floppy disk.
I honestly can't speak for the HD20 external hard drive. The bottom line that Apple determined was an acceptable limitation was: To install on a Mac Plus, you needed two external SCSI hard drives, or possibly two partitions on one external hard drive. You needed one SCSI external drive to boot at a minimum System 7.5, so you could run the 7.5.3r2 installer to install that OS on the other SCSI external drive. I'm going to presume that's the same requirement to install 7.5.5.
The way we did it, in general, was to use another, newer Mac, like an SE/30, LCIII, or Mac II or whatever, to use the 7.5.3r2 installer to create a univeral install on an external SCSI hard drive. The universal install just installed EVERYTHING, all the software components for both PPC and 68K Macs, all the model-specific components; everything. As a result, it would boot any supported Mac. It was a magic bullet for a problem like installing on a Mac Plus. You had to be careful to get your dual external SCSI hard drives terminated correctly, but once you did, you booted off the Universal OS on the external, then launched your 7.5.3r2 installer, which could be on the Universal boot drive (very convenient) or could be on an external CD drive (more complex for the SCSI chain), or it could be on floppies (which are 1.4Mb so won't work on a Plus). You'd select the second external drive as your target for install, and let it rip. You could just use a bootable System 7.5 on the boot disk. You also needed the installer, and one way to do that was to copy the CD files to the bootable external, by using a better/newer Mac with a CD drive to read the CD and copy the installer to the bootable external SCSI drive. The QA testers were generally each assigned an external hard drive, and we'd typically install a Universal 7.5.3r2 install to use as the boot system, and copy the CD contents to the drive to use as the installer. You could take that to any Mac and have everything you need to install, but the Mac Plus and dual-flopy-drive SE additionally needed an external target drive to install on.
Another interesting note: The 7.5.3r2 installer can run over a LocalTalk network. It's SUPER slow, but it will work. You can connect to another Mac that has the installer on it, and launch the installer that lives on the remote network computer. The Mac Plus supports LocalTalk, so in theory that should work, but it didn't, and I wrote up that bug. Apple decided to not fix that bug (or decided it couldn't be fixed; it might have been some unique limitation on the Mac Plus) but the result is that you can't install on the Plus using an installer over a LocalTalk network. That's not really a major loss because even if it did work, it would take a REALLY long time.
In conclusion, the best way to install 7.5.3r2 on a Plus, and by extension 7.5.5, is to use a newer/better Mac to set up an external bootable drive with at least System 7.5, but more commonly a universal install of 7.5.3r2, along with the 7.5.3r2 or 7.5.5 installer files or images, and also connect an external SCSI target drive, with proper termination. Separate partitions could be used on a single drive, if you wanted to do that instead.) Boot off 7.5 or newer, launch the 7.5.3r2 or 7.5.5 installer, select the target disk, and install away. Once you're installed and shut down, you can remove the boot/installer drive, leaving just the target drive (with proper termination) and use that with your Mac Plus.
I have the retail 7.5.3r2 installer CD, and I have a Mac Plus that I use with BlueSCSI. At some point in the near future I'll get around to experimenting with this more, and I'll update with anything I find with 7.5.3r2 or 7.5.5, but as previously noted by others, a Mac Plus is really at its best with System 6.0.8.