Jay1 wrote:1: Will meditation lead me to poverty? If I let go from my attachments, will I end up like a homeless man as I will not desire a home anymore?
Only if that's what you want to do. If anything, meditation might provide some insight which will challenge some of your pre-existing notions... so your perception on the various pros and cons of certain lifestyle choices might change, but the choice will always be yours to weigh up.
Jay1 wrote:1.5: Can a Buddhist be ambitious?
Sure. Monks generally strive towards becoming an "arahant", and there's not much more ambitious than that. Lay Buddhists can do whatever they want, although they ideally strive to maintain the five precepts.
Jay1 wrote:2: Is belief in rebirth necessary? I see no reason to believe in it, so...
See MN 60 - Apannaka Sutta... or the section from "Buddhism For The Modern Skeptic" on rebirth... both are easily found online via Google.
Jay1 wrote:3: I know that monks are prohibited to listen to music, should I stop listening to music myself? If not, then why is it a bad idea for monks to listen to music but not for me?
For monks, or for those on intensive meditation retreats it may be a distraction from their intended goals. Is music in conflict with your goals?
Jay1 wrote:5: Oh, and what teacher would you recommend? Apparently Ajahn Chah and Mahasi Sayadaw are supposed to be good? Are they? Btw, I'm a Christian if that matters (I've heard that Buddha was apathetic to the question of God's existence)
Well Ajahn Chah and Mahasi Sayadaw are deceased, so if you're allowing the deceased into the equation you may as well go with "The Teacher", aka the Buddha... whose teachings are preserved in the Sutta Pitaka.