Yes, you can have multiple 'dialer map' statements that specify which number to call according to the distination IP address (of course you need matching routes to those desination IPs as well). You can also get a little more fancy/flexible/involved and use dialer interfaces.
Yes, you can dial into the network using analog lines. You can tie a modem to an async interface (such as the aux port). I'm not aware that there are any WIC cards that interface directly to an analog phone line. You can make the serial ports on the WIC-1-T or WIC-2-T async and tie those to modems. The 1700 series wasn't really designed for lots of remote dial-in users though.
I'm not clear on that last part. If your server needs to reach an IP for whatever application and has the 1721 set a the gateway, you set up the router as above in the first case. If you are talking about having the 1721 dial an actual fax machine on behalf of the server, that isn't going to work.
I would recommend that you spend some time researching these moderately complex configurations on CCO. There are lots of explanations and configuraiton examples for everything you need help with.