I have tried all of the setting combinations as a result of what I'm seeing in this thread and have not experienced the dropping out problem... ever. I have settled on Energy Savings On with Always Connected ticked because I don't like the delay when I get in the car if it's sleeping (during the day) and sometimes have trouble getting the mobile app to connect if the car is sleeping and/or if the mobile access has "gone to sleep".
I use Slacker continuously and use Satellite View on the maps all the time as well. The car will be on WiFi in my garage, but flips over to 3G seamlessly as I set out with no interruptions to either Slacker or the maps.
What I can say is that if I do a re-boot, it takes the 3G a very long time to come back. The system will be up and running, Bluetooth will connect, but it takes a very long time for the cellular bars to come back, then a further long time for the 3G icon to appear. The whole process may take 10 minutes. But this is when I have initiated a re-boot.
Another observation is this: On my commute between the Toronto area and the Waterloo Region (in Ontario) there is a spot on Hwy 401 just west of Milton where the 3G signal is very low. On most days it's fine, but if it's raining I will sometimes get a 3G drop out. I assume the rain is weakening an already weak 3G signal. It's always in the same location so I am sure it is a signal strength issue and not the car doing something weird. Once the signal is restored as I drive out of the weak signal area (and again, only if it's raining), Slacker and the maps come right back.
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Those are my preferred settings, and I don't seem to be having any issues. Energy Savings On only causes the car to sleep at night, so I don't often get in to the car when it's actually sleeping, but I have, and have not experienced any connectivity problems.