Ok, I'm just trying to map this out to my knowledge so that people can give me advice on what to studie up on next.

So you use telnet to connect to whatever your trying to access. Try different ports until you find one you can access.
At this point i'm a little blurry.
Do you need a cracking program specific to the Hardware/software of the other comp.?
How can you tell what they are running? Etc.?
Also I've found different programs purported to "Hack" different email site (Hotmail, etc.) Now my question is not how, it's simply are there methods to do this that do not involve just entering password after password until you find the right one? ( with or without a program.)
I'm pretty much to the point at which I can find and connect but, now what?