IMHO, I think the boot-to-charging mode's a little shakey - If I plug in power when it's off, It will semi-boot and charge. I'll have to unplug the power and wait a minute or so before I can actually boot into maemo.

I suggest simply leaving it on all the time - It uses almost no power in it's sleep mode, and is a lot happier that way.
Just leave it on, plug it in, and in the morning unplug it and off you go.