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DAW vs portable multitracker, please help a newbie

Hi guys, new guy here.

I'm currently using a Korg D16 and I'm ready for something better to record our band. Don't need pro quality, but would obviously like to get the best I can afford. My budget is $1500~$2K.

As the title suggests, I'm torn between a new stand-alone workstation, which I'm quite comfy with, or a DAW, which I know nothing about.

Portable decent active monitors.

I need a pair of monitors to be taken with me for recording sessions. I have Adam P11's at home, and I'm not going to take them with me. Small monitors would be adequate and easily portable. So far I listened to:
-Roland 10 (good bass, lack of midrange, harsh treble)
-Edirol MA-7A (Good treble, lacking mids, no bass/exaggerated bass)

Portable stereo recording gear from small recital to orch.

I am looking to start recording concerts, recitals, audition tapes, demos, etc. It would be all classical intruments. I'm looking for some kind of gear to record just stereo (i don't wanna get too fancy with tons of mics and wires running all over the place).