Awarding top OurStage artists 1-on-1 sessions and opening spots with industry veterans:

1. What are the most important things to pay attention with considering
signing with a label?
I think you need someone in a position of power there that's a real champion of your music. If it's a small label, it should probably be the boss. If it's a big label, then it should be someone that's pretty far up on the totem pole. They might get fired eventually anyway, but at least for a while you'll have someone with some power rooting for you. Also, have they had some success with someone in your genre? You don't necessarily want to be the guinea pig.
2. What should a new artist expect from a Manager? How can you tell a good one from a bad one?
You should check a manager's reputation to make sure they don't tend to annoy everyone they work with. This is actually the case with a lot of young managers. Other than that, I think overwhelming enthusiasm and common sense are the most important assets...they don't always need to have a long track record to be a good manager.
3. While coming up, what artists/band did you seek to emulate and why?
Musically, our ultimate heroes were always the Beatles. But when Chris and I started to play music together there were many other artists we "emulated" musically...The Beach Boys, Zombies, Steve Miller, The Cars, Squeeze, Elvis Costello, Crowded House, Aztec Camera...etc. Just because we liked their music. We never really thought to imitate anyone business-wise...although you did see bands like REM who were afforded the time to grow really slowly over a long career until eventually they were huge. That's less common these days, it seems.
4. What is the most important to consider when interacting with fans of your music?
Don't be an asshole.
5. How important is having a lawyer in the music business and if you have one where did you find them?
A good lawyer can be a good first contact inside the industry if you don't already have a manager or label. Usually a recommendation from musicians you trust would be a good place to find a lawyer...or you can find their names on the liner notes of CDs you like (do liner notes still exist?).
6. Are there any specific things you've done to avoid big business and the music industry?
I've mostly worked with labels rather than independently, but that may be a function of my age...I think everything is really changing now.
7. Is it possible to make it big without a major label?
Definitely it is now. The big labels are becoming less and less relevant yearly. And they no longer have a lock on distribution or on promotion thanks to the internet.
8. What's the best things to spend money on (recording, publicity, tour, managers, lawyers, etc.)?
A good publicist goes a long way! So does some good indie radio promotion. And of course nothing builds a fan base more than touring, so play as much as you can. Recording doesn't need to be expensive these days, but don't put out anything that sounds like crap if you can avoid it...it's worth spending as much as you need to to make your music sound good. Otherwise, nothing else you do matters.
9. What's the biggest waste of money?
Blowing all your money on tour by staying at fancy hotels, etc...i.e. living like a bigger rock star than you are. You come home with nothing if you're not careful.
10. How has the Internet changed the way you approach building a fanbase?
It's the tool everyone uses to find out about the bands they like, to discover new bands, etc. It helps keep people feel like they're up on what you're doing. With very little effort you can build and maintain a fanbase online, compared to the old days of "mailing lists" etc.