my $.02 after owning many BMW's
1. V8 vs. I6. Both are great motors and essentially bulletproof. I6 is smoother and quieter and will be very capable as a daily driver and will cruise without stress on the highway at 80-90mph all day long. The 4.4 gives you the torque many desire for around-town sprints and better towing capacity. Mileage is about the same between both. Maintenance can be slightly higher on the V8.
2. You will want the Premium and Cold weather package at minimum (I see you are in CO). Sport package adds upgraded wheels, suspension and steering wheel. I prefer a tighter ride, thus I look for the Sport package. The standard suspension is fine if you want a softer ride.
3. NAV - it's outdated and DVD based. I personally would not want one because my Garmin is superior. NAV on resale of a 4 - 5 year old car does not effect the price or choice in my opinion. If you are a heavy iPod user, it might benefit you for the display. If it has NAV great!, if not, it's no big deal .....
4. CPO - if you are not good at turning wrenches or have a good BMW certified indy in your area, CPO is probably worth the money. There are many praises and dissapointments with CPO's and extended warranties on this sight. Do some research. I personally have never bought one and been just fine. Maybe luck has been on my side
5. Take your time, prices have dropped quite a bit in the last year and there are some good deals to be had.
6. Most important *** check the maintenance history *** and have the car inspected BEFORE you buy. These may be the ultimate driving machine, but poorly maintained, they can be the ultimate money pit. Expect 150K - 200K miles on a well maintained BMW.
Good luck and enjoy you BMW ............