I'm still a newb at this, but got my system up and running with only two minor bugs.
1) The caller ID from both lines is the same. Not sure how this is as I triple checked (and got a friend to double check) every field in the Extension, Outbound Routes, Inbound Routes, and Trunk menus and they both seem correct, each with their different CID and password (when applicable). Both extensions have their own inbound route, outbound route, and trunk so there shouldn't be a mixup anywhere. Whether I use a softphone or an ATA adapter, I still get the same outgoing Caller ID from both lines. If I call each line from outside, I can reach both lines using their own numbers without a problem. If you need more info, I can post a config file info. Just let me know which one you need.
2) I'm still super new to dialing plans. I had to adjust the delay on the ATA converter because it wasn't enough time to dial all of the numbers before it gave a fast busy tone. Anyway, in my city we have 3 area codes that are all local, so dialing 10 digits is the norm. I need a dialing plan that adds "#" after 10 digits are dialed so it sends the call through immediately, even after 1-8xxx number (toll free) or 911. I would also like to add an "#" after the three digit extension. First, do I put the dialing plan in the outbound route or the trunk? And second, what exact dialing plan should I use. I kind of get the jist of it but not enough to be sure I know what I'm doing.
Thanks in advance for any help guys. I'm tearing my hair out here.
P.S.
If someone can really help me out. I have a couple of different Windows 7 product keys from my Technet account. They're licensed for testing purposes only so I can't sell them, but they're really the same as a retail key. Help me make this work and I'll give you one.

1) The caller ID from both lines is the same. Not sure how this is as I triple checked (and got a friend to double check) every field in the Extension, Outbound Routes, Inbound Routes, and Trunk menus and they both seem correct, each with their different CID and password (when applicable). Both extensions have their own inbound route, outbound route, and trunk so there shouldn't be a mixup anywhere. Whether I use a softphone or an ATA adapter, I still get the same outgoing Caller ID from both lines. If I call each line from outside, I can reach both lines using their own numbers without a problem. If you need more info, I can post a config file info. Just let me know which one you need.
2) I'm still super new to dialing plans. I had to adjust the delay on the ATA converter because it wasn't enough time to dial all of the numbers before it gave a fast busy tone. Anyway, in my city we have 3 area codes that are all local, so dialing 10 digits is the norm. I need a dialing plan that adds "#" after 10 digits are dialed so it sends the call through immediately, even after 1-8xxx number (toll free) or 911. I would also like to add an "#" after the three digit extension. First, do I put the dialing plan in the outbound route or the trunk? And second, what exact dialing plan should I use. I kind of get the jist of it but not enough to be sure I know what I'm doing.
Thanks in advance for any help guys. I'm tearing my hair out here.

P.S.
If someone can really help me out. I have a couple of different Windows 7 product keys from my Technet account. They're licensed for testing purposes only so I can't sell them, but they're really the same as a retail key. Help me make this work and I'll give you one.