Configuring dial-up OOB management

Hey guys, long time no see!
For the past month or so I've been trying to figure out how to get a modem to work with a router so that I could dial into the router for out-of-band management. The issue that I'm having is that I can connect to the modem, but then I get no router prompt. From what I've read, you can connect the modem to either the router AUX port or the console port, with each having their own advantages and disadvantages. But regardless of which I connect the modem to, how I arrange the DIP switches, what modem init strings I use, or what AUX port config (i.e.: speed, flow control, etc), I only get as far as being able to dial into the modem...but not getting a router prompt. What in the world am I doing wrong?

This is my setup:
Laptop with internal modem port ---> phone line ---> phone port ----> PSTN --->phone port in my apartment ---> phone cable ---> my modem --> DB-25 serial to RJ-45 rollover cable ---> router console/aux port.

Is this the right setup or do I need a modem on each side? Just to be sure, I configure the modem that connects to the router with the init string, right?

My modem is a U.S. Robotics 5686. I'm testing on a Cisco 2511-RJ and 2510XM router. In a little bit I will try on a 3550. Ultimately, this will be implemented on 4500s and 3900s.

I think the issue is a mix of my not knowing enough about such an archaic technology, there not being enough information on the Internet (because it's so old), and there being too many points of failure (i.e.: router config, DIP switch arrangement, modem init string).

Thanks for your help