tbh, i don’t even know what remote debugging is supposed to offer 
i just got sick of the process of getting the script to run in rhino to see if it works (and doing that process a hundred times an hour)… but so far, rhino seems to tell me where the errors are happening and in many cases, why it’s happening… so that’s sweet.
here’s a pretty ch_easy little workaround to the switching problem:
( http://youtu.be/CGWUnuiVix0 )
managing the files will need a decent game plan but i think if you have 2-3 files just for the switching/writing/copy&pasting/etc then using Duplicate(or other methods), put them in ‘real’ files when need be, it should work out ok…