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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)