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I thought that setting would stay set until you change it, not depending on boot up. If in fact it doesn't work that way, use "Brightness Level" widget from Curvefish in the Market: https://market.android.com/details?id=com.curvefish.widgets.brightnesslevel&feature=search_result I've been using it since I got my phone and it works fantastic. Set it to exactly the level you want and it stays that way with an indication on the home screen of the percentage.
Could be. You might try a factory reset even though those are a hassle. It's what Verizon tech support would have you try before they would exchange the phone anyway.
This thought just occurred to me. Have you installed any apps that might also control brightness? Maybe there is an app overriding the system setting.