So I've had a little more time to spend with this and I tried out Realterm as well. Still no luck.
Roomba status will allow me to turn on my roomba but it just stays in passive mode and 'connecting...' as the sample count goes on and on and on. Pressing movement enables full-mode but that still doesn't do anything. Althewhile my usb-to-serial's transmit light is blinking.
Again, everything on the port side is configured correctly, my Usb to Serial's port is 4, baud rate is 57600, parity set to none, data bits to 8, stop bits to 1 and hardware flow control to none.
Now if I try out Realterm, it sees my port but here's where I get a little lost. If i start it up with the usb to serial board plugged in and connected to my roomba, it sees the port but the status does nothing except blink a yellow TXD if i type in a string and hit send numbers (I'm using '128 132'). This also causes my transmit led on the usb to serial to blink once. Now if i unplug the usb to serial port from my computer and plug it back in again, Ring, DSR and CTS will begin to blink. I transmit the same string again and it does nothing. Realterm claims it transmits but no light up on the Usb to serial and no action out of the Roomba.
To rule out whether its the usb to serial connector or the roomba, I'm going to run the TurnBump sketch in arduino and see if that actually does anything.
If anyone has any thoughts of something else I can try (or a step I've overlooked), I'd appreciate it!