Re: SSH Login
I think you hit the nail on the head with NetworkManager. This is a real problem IMHO. I'm not certain of the exact commands you'll need, but something like this added to /etc/rc.local might get it going, substitute your wireless interface for wlan0:
ifconfig wlan0 up
iwconfig wlan0 mode managed essid your-esssid-name
This assumes you have a wireless router operating in managed mode with a dhcp server running, more or less the usual case.
This will probably need some tuning and there may be adverse consequences when NetworkManager starts up later! Good luck!
There are no dumb questions, just dumb answers.