#1
Alright this is going to be a rather massive undertaking for me, and I must admit my level of knowledge in this area is extremely limited.

First, what I'm looking to do:

Recording: Fairly minimalistic really. I've written a bunch of midi backings (drums/bass a bit of piano) and I want to be able to record some guitar and vocals over top. For guitars, I want to record from my amps, and not something like the Line 6 toneport.

Live: Well currently I've been using a Boss DR-880 as backing when I play live, and I'm finding it doesn't really fit my needs. It doesn't have nearly enough memory, and the sound quality isn't as good as I'd like.

So, I'm basically looking for some kind of rig that will give me good sounding midi backtracks, as well as tracks I've recorded.

----

Now I'm starting with a pretty much blank slate here, and I'm willing to spend the money required to put together something that meets my needs.

So...

Computer? Mac, PC? I've fooled around with some recording stuff on PC in the past. Always had rather massive problems with programs crashing, sound card issues and whatever else.

Software? The easier to use the better, something with a large support base would be nice

Audio Interface for recording? Interface/controls for live sound?

Anything else? I've already got mics cables a PA and all that.
#2
Have you looked into Logic much? You could use Logic for recording and your backing rig (Mainstage). All you will need is the Macbook, Logic, a basic interface and a controller of some sort.
Gear:
Ibanez RG4EX1
Laney VC50
Roland Cube 30X
Boss MD-2

Ibanez GSR200

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#3
Frankly, with 15 years of one man band pub gigging, having taken it from Roland RAs with floppy discs, I eventually brought it down to 2 different rigs:

- an mp3 player through a mixer,

- a touchscreen toughbook (programmed to control everything from the touchscreen, no mouse, no keybaord), with a lightweight multi-track software and a 2 channel usb audio interface, through a mixer.

There's no killer solution, just a lot of live tryouts and plenty of mistakes done.

For playing 8-12 tracks mixed down to stereo, a full ruggedized panasonic CF-28 1GHz pentium 3 rugged toughbook (can take falling, beer spills, cigarette ashes, stomping) works wonders. They go at $200 on Ebay these days.

http://www.youtube.com/watch?v=ckIV1MhGbXo

Have a look at Quartz Studio here:

http://www.digitalsoundplanet.com/SoftwareHouse/Products/Quartz_Studio/Studio_Pro_DSP/Comparison_chart/comparison_chart.php3