Couple of ideas - first, insert a sensor before you go to bed, connect all parts, make sure the Dex has the "i am communicating" indicator in the bottom corner, but DO NOT start the new sensor. In the morning, then hit start and the dex will go through the 2 hr start as normal. Sometimes it takes more than 2 hours for the sensor to get acclimated to you and I am finding as a new Dex user that if I wait to start I get way better results the first day.
Also maybe make sure you are inserting the sensor in an area that has a bit of a "pinch" and not in a real lean body part. That too may help.
If you get bleeding (happened one time on me, horrible bruise but was able to save sensor), wait before starting, may try "massaging" around the sensor site, just be real careful that you do not tug/massage to hard. I think that helps to break up blood, as Tech told me that if blood sticks on the wire the sensor may fail. I also used warm, wet cloths over the sensor then, and even a heating pad on low heat for about 15 to 20 min. Got two weeks out of that one even with soreness the first 3 days!
Good luck! I hear you, I just read instructions, watched video and began. Lots of time w/tech on the phone, but sure beat having to wait for appt. w/my diabetic educator - would still be waiting! LOL!