What do I need to do??? Couple of ??'s

I'm 25 years old, 5'10 220.  I need to drop at least 30 pounds.  I just started to lift weights.  I have a couple questions regarding this.  I got a membership to the Y. 

1.Is it okay to start out on machines or should I do free weights?

2. What kind of foods should I eat when trying to build muscle?  Can I build muscle and lose weight at the same time?  I'm weak, what is the best way to gain strength?

3. Should I take any supplements?  Not for weight loss, but building muscle.  I don't want to take steroids or anything like that.

4. How many times a week should I lift?  How many sets and Reps to build muscle and lose fat?  How much Cardio?

If anyone answers me, I'd be greatly appreciative.  If any of my questions are dumb I'm sorry.  I'm very new to this.   I just want to make sure I'm doing things right.  So many books tell you different things.  And I don't want to waste my money on supplements that don't work.  Thanks for any and all advice.

One other question, is it possible to get rid of cellulite?  What is Cellulite and how do you get rid of it?  This isn't for me, but my girlfriend, she's really skinny, but has a tad of cellulite on the back of her upper leg where it meets her butt?
 
Thanks for any info guys.