Just a quick comment. I occasionally use cygwin but don't know how close to a real unix shell it is.

1-With a real shell the directories are searched in the order they are found in the path statement.
So PATH="/a:/b/1:etc..." the /a will be looked at first.

2-Dont forget to EXPORT your path! About once a week I work an extra 15min on a problem because I forgot to EXPORT the varaiable.

3-You may not have complete control of the path under Cygwin because MS Win may do some of its own hunting before the Cygwin path statement takes place. You will have to do some quick tests

I hope this helps you consider some options....
JZ