I just went through similar decision process. I sold my old compressor on craigslist within hours. I probably had 20 inquiries afterwards to. They bring good money as long as they are in good operating condition. You may be surprised that you can get about what you probably paid for that Kobalt back out of it. I wouldn't be surprised at all if you could get 300 or so for it.
Spend some time over on GarageJournal. Tons of compressor info over there.
They say Quincy makes a really good compressor if you can spring for it. A 2 stage 5hp(running) would be a nice setup for a home shop and likely more than anyone would ever really need. You just have to make sure your wiring is able to support the draw of the larger motors.
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John
'71 Nova ( Build thread)
FFR Roadster
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