Assumptions
The documentation for the Classic ASP system is rather light.
Management is not looking for a rewrite.
Since you have been doing ruby on rails, your (VB/C#) ASP.NET is passable at best.
My experience
I too inherited a classic ASP system that was slapped together willy-nilly by ex excel-vba types. There was a lot of this stuff <font size=3>crap</font>
(and sometimes missing closing tags; Argggh!). Over the course of 2.5 years I added a security system, a common library, CSS+XHTML and was able to coerce the thing to validate xhtml1.1 (sans proper mime type, unfortunately) and built a fairly robust and ajaxy reporting system that's being used daily by 80 users.
I used jEdit, with cTags (as mentioned by jamting above), and a bunch of other plugins.
My Advice
Try to create a master include file from which to import all the stuff that's commonly used. Stuff like login/logout, database access, web services, javascript libs, etc.
Do use classes. They are ultra-primitive (no inheritance) but as jamting said, they can be convenient.
Indent the scripts properly.
Comment
Write an external architecture document. I personally use LyX, because it's brain-dead to produce a nicely formatted pdf, but you can use whatever you like. If you use a wiki, get the graphviz add-in installed and use it. It's super easy to make quick diagrams that can be easily modified.
Since I have no idea how substantial the enhancements need to be, I suggest having a good high-level to mid-level architecture document will be quite useful in planning the enhancements.
On the business logic unit tests, the only thing I found that works is setting up an xml-rpc listener in asp that imports the main library and exposes the functions (not subroutines though) in any of the main library's sub-includes, and then build, separately, a unit test system in a language with better support for the stuff that calls the ASP functions through xml-rpc. I use python, but I think Ruby should do the trick. (Does that make sense?). The cool thing is that the person writing the unit-test part of the software does not need to even look at the ASP code, as long as they have decent descriptions of the functions to call, so they can be someone beside you.
There is a project called aspunit at sourceforge but the last release was in 2004 and it's marked as inactive. Never used it but it's pure vbscript. A cursory look at the code tells me it looks like the authors knew what they were doing.
Finally, if you need help, I have some availability to do contract telecommuting work (maybe 8 hours/week max). Follow the link trail for contact info.
Good luck! HTH.