How I started is a long story, so I won't get into it now. But I was given my first gig initially, the club liked the show they hired me permanently & added 2 more nights. Then a couple other clubs came in & saw the show & hired me for a couple more nights - working 5 nights within a 1 month period from starting without looking, this is not the norm when just starting out, I got lucky.
Honestly wouldn't do a free show, once you get a rep for that you will be deemed either cheap entertainment or screw yourself for any kind of possible money raise. You could go in with a set price, then negotiate a starting price for say 4-6 weeks with an intent/promise agreement from the bar which after that you either get your price (provided the clientelle are coming & the ringout is good - if not then you can renegotiate or determine that karaoke may not be right for that club) or you walk! & then follow through.
Never solicit a place that already has karaoke - especially if it's already good show. It automatically gives you a bad rep. & it's nicer to work WITH other companies than against them. If a bar calls you looking to replace, then I personally see it as fair game & would set up a meeting.
I would get a promo pack put together, an about you with on your letterhead, maybe with a scaled down version of your book/selection (mine had no number & 3 column print to condense to a manageable size), maybe an overview of your equipment (not that most bars care, but some still might), any kind of print ad's ideas, web advertising, website if any (MySpace is pretty popular free choice to begin) & how you will promote the show to attract customers.
Just a few ideas.
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