You should cover artist and songs you like. Find material that you can make your own and execute as well as the original or better. Material that is similar to your style. That way when you do originals, it's not so far out there. Avoid the obvious if possible, like "sweet home alabama", 'ball and chain", etc..... Take a look at your influences, pick 1-2 songs from each. Find the single and another cool tune that a few may know and go from there. Be carefull, it's easy to get lost in paid cover gigs and forget why you started. My advise, find a few cover gigs, but keep pushing the original showcase venue more and more. Your young, just keep playing!!!!!!! Gets tougher when you're older with kid. Free time is limited and you're always tired!!!!
Oh by the way, Happy Thanksgiving!!!!!!!
We should get together one of these days.

willy
 

Having listened to literally thousands of covers and hundreds of originals from indie artists, I'm gonna chime in with my two cents' worth.
From my perspective, I love to hear the art behind the cover. What I mean is, you're an artist... paint the Mona Lisa if you want to, but if you're Picasso don't try to copy Da Vinci brush stroke for brush stroke. Best example from just this past week, I listened to a cover of 'Creep' by Radiohead performed by Justin Sanders (who I think sounds a little like George Michael) while accompanied by a ukulele. Yeah, it was a cover, but Justin crafted it HIS way. Play the song, but interpret it the way you would have done it if you had it to do first.
From the paying venue's perspective, they want customers to stay put and spend money. If you can play something that's a standard that they'll sing along to, they'll stay. Again, best example from just this week (same night in fact) was Danny Maika performing 'Sweet Caroline', the old Neil Diamond classic. Every time he got to the chorus and sang "Sweet Caroline", he had half the crowd chanting "Bom bom bom" before he belted out "good times never seemed so good". And he also played one of the all-time best sing-along songs, 'Brown Eyed Girl'. He grabbed 'em and made them part of the show.
I do agree with Wilfax that you have to play what you're comfortable with, but I would never settle for a paint-by-the-numbers approach if I had talent like yours. And of course, if I can help you in any other way with the paying gig thing, I will.

See you soon!

-GB
 

songs to make your own:
Mustang Sally
At Last
Dark End of the Street
Try a Little Tenderness
Kate
I Can't Stand the Rain


those are the few off the top of mah noggin...more to come latersauce when i can actually do some good thinkin'.
Happy Thanksgiving!