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Setup For Whisky

I agree to save for a better amp first, and a DI, but as far as compressors go I think the BBE Opto Stomp is one hell of a deal. You can get it brand new on Amazon for a cheap as $65. Or buy used, then you can sell it for the price you paid when you're ready to upgrade. I love it for a 'set and forget' compressor. Most built in compressors on amps aren't that great.
 
My band never had to "pay to play" at the Whiskey, the Roxy, or the Troubador. We didn't get paid very much, and the $9 bottled beers were ****ing recockulous, but we never had to pay to play.

The band I tech for plays the Roxy in May, not paying for it. Played the Viper room last fall and i think it paid a couple hundred. not exactly sure. Sometimes pay-to-play can benefit you if you have merch, which can help cover the cost if not blow it away completely.