You need to install a bunch of gems locally since the Remote Installation didn't work or at least not stably.
By assumption that instantrails2.0 is ready on your xp platform, then you cocould go on the following steps:
1 download netbeans6.8, Which is a wonderful IDE for Ruby world, download it freely here:
Http://netbeans.org/downloads/index.html
Remember download the ruby one, which is around 92 M.
2 download all related gemsFor debugging Ruby. Here is the list (please google them by names ):
15,360 columnize-0.3.0.gem
31,744 linecache-0.43-mswin32.gem
Ruby-debug-0.10.3.gem 117,760
113,152 ruby-debug-base-0.10.3-mswin32.gem
Ruby-debug-base-0.9.2-mswin32.gem 36,864
Ruby-debug-ide-0.4.6.gem 31,744
The order of installation is columnize-> linecache-> ruby-debug-base-> ruby-debug-ide
3 launch netbeans, New project with existing Ruby project codes, for me, I import redmine project.
Note that the build-in Ruby platform is JRuby-1.4.0, you get to change it to Ruby 1.8.6-p111 which shoshould be installed under your instantrails2.0/Ruby.
Anyway, by clicking tools-> Ruby platform, if you see quick debug engine of Ruby is(Ruby-debug-ide)
then Ruby debug enviroment is ready for you, you coshould set breakpoints/step in/step out/run to cursor just as what you coshould do with Java/C ++ codes.