For your budget, there are some amazing Ktm 990's on the market, as the 1190 has come in. I started biking 3 years ago and went straight onto a 990. Did intermediate course at Staals Amersfoort and then went straight into a 2 week tour through Bots, Zim and Moz, mainly offroad. Taking it slowly and practicing the things I learnt, I was comfortable within a few weeks.
My suggestion, for GF and you, 990 but must do course on how to ride Pillion and then practice in parking lots, vacant roads, etc. If you go the 690, 650, etc way, you no safer unless you do the above.
Either way, do some lessons, practice on weekends silly things like slow turns with GF on back, emergency braking, jumping potholes, etc. Safer rather than sorry. Good luck.