The ME machine will probably work fine IF you have an RSS version that will work with Windows 95/98. I have version R03.02.01 28-Jun-96 working well in ME for the past 10 years, so that and any later versions should work, BUT there are some steps you'll have to take after installing it to make it work properly. Below is the short version of the "read me" file in the later software, and in it you'll find the long version of these settings. If your copy of the RSS does not have these instructions, it's still likely to be a version that will work with 95/98/ME if it's later than the one listed here or has the update for 12.5 kHz channel spacing, so be sure to follow these steps below before attempting to program at home or you're likely to become familiar with the term "brick." If you are able to read the radio after making these mods, then it should also program just fine provided that there's no "noise" getting on the cables. That's another problem that these setups are susceptible to.
After installing it, go to Explore and call up the file so that the files are displayed in the right window.
Right click on the HT1000 application icon (should read Type: Application Size: 474 kb when you mouse over it)
Left click on Properties.
General page: Change "Attributes" to Archive, make "Read only" and "Hidden" False
Program page: Change "Run" to Maximized.
Make "Close on exit" True.
Make "Prevent MS-DOS-based programs from detecting Windows"
True.
Font page: Choose "Both font types."
Memory page: Make all choices "Auto."
Screen page: Usage: choose "Full screen." Initial size: choose "default."
Window: make "Restore settings on startup" True.
Performance: make "Fast ROM emulation True.
make "Dynamic memory allocation" True
Misc. page: Foreground: make "Allow screen saver" False
Mouse: make both choices False
Background: make "Always suspend" True
Termination: make "Warn if still active" True
Idle sensitivity: Low (all the way left)
Other: make "Fast pasting" False
Windows shortcut keys: may be left True
Again, all of this is per the supplemental instructions that came from MotherMoto to use some RSS versions with 95/98, and which was in the "Read me" files in later RSS versions, so if you have the version with the updated "read me" file, you'll find all this in there.