1) I use a Mac , so I can't advise you on software for windows machines.
2) X10 is for the DIY'er and you need to learn about a few things before installing. Such as RF interference (cordless telephones etc.), power line noise (computers, TV's, etc.), range (metal in walls etc.), phase coupling (getting the signal from one phase of your wiring to the next) (plug-in coupler about $20) and which house code/codes will work best for you. These are all very simple things to learn about and will save you a lot of time & effort.
Here is an example of house codes and reliability:
Don't use: A or M
Most reliable: C, F, G, I, J, L & O
Maybe OK: B, E, H, K, N, P.
3) First make a map of your house wiring.
Which breaker controls what ? Makes troubleshooting a lot easier.
4) X10 can be and is reliable if set up properly. I have my home, detached garage, lawn sprinklers, automatic gate and even my dog fence set up. A year now & no real problems.
5) The X10 web site sucks but there is lots of help on their forum: I'm not allowed to post a link here. But, go to the X10 web site and click on Forums.
Hope this helps you.