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In terms of software I started with Guitar Rig 5 Player, quickly bought the Rammfire upgrade, then bought the Pro version of Guitar Rig 5 in a Native Instruments half price sale. Then I stopped playing with it because I found I preferred the simplicity of my Cornell amp. Last year I bought Ableton Live and run Helix Native as a VST plugin into it, which is entertaining.
What operating system are you using? If you're using a Mac, then Logic Pro X has some nice built in guitar sims, and you can also record with it! I recorded my riff of the month entry using the "Brown Head" sim with all EQ set flat. It's a little bright, but overall, for a built in amp sim in a DAW, I can't complain.
http://thefretboard.co.uk/discussion/128746/raw-riff-of-the-month-rrotm-35-chat#latest
From what I can see, that lead won't give you a midi input. It's purely phono to usb, with no midi converter anywhere.
Does WIn10 recognise the lead when you plug it in to a usb port? Does anything install/activate?
I've not used GuitarRig, but I'd guess that you need to hunt through the settings and look for audio input. Then check that Win10/GuitarRig has recognised that you've plugged something (capable of delivering an audio input) into your system.
http://www.ikmultimedia.com/products/irig2/
Suitable for phone/tablets (iOS/Android) . Don't think that I'd use it on a phone, but if you've got younger eyes, you might be OK. Perfect if you've got an iPad or Android table about the place though.
Easier to use, apps are better/cheaper, and you can plug & play wherever you want rather than being tied to wherever the PC sits.
iRig isn't the best interface, but it's easily within your budget and is a good place to start. Spend the rest on some apps when you get bored of the free version of Amplitube (which includes some fx, amp sims, etc, IIRC) that comes with iRig.
You really want the sort of speakers that fit over your ears.