#1
I would like to be able to plug my guitar into my laptop, (no not shoving the cable into some makeshift hole) something with a usb end, that i can use to record onto any synth software. I tried something from behringer, but i came across too much of a headache with error messages when trying to install it, and with their tech staff not knowing what the **** to do

Does anyone have any suggestions of a device that they use? or have had good experiences with
#2
You need either a stealthplug, or an interface. Line 6 has a pretty cheap interface for about $150 that comes with Ableton light and the demo of Pod Farm.

It's decent for a first interface.