Re: item 1, if it's an area you are familiar with and you know that you will need to be on the small chainring eventually, start there, even though it may feel too "spinny". I'll bet if you had a cadence meter you'd find that it really wasn't all that spinny. And you don't have to deal with the anxiety of chain mishaps in the middle of a hill that you definitely don't want to stop on. I know that the higher gears on the small chain ring can be rattly too, but if you need to be in lower gears you'll probably shift out of that pretty quickly.

What cog are you on in the rear?

But if it's territory you are unfamiliar with, try shifting to your lowest gear on the middle chainring (I assume you have a triple) and standing. I do this a lot, mostly out of laziness, but I've found that it actually gives my legs a little break...I ride much more slowly. If I need to I grit my teeth and tighten my abs and tell myself that I'm working on core strength.

Finally, always look ahead. If it looks steep, get on the small chainring. And if it ends up not being all that steep, there's no crime in spinning up in a higher gear on that chainring (unless of course you're one of those "triples are for wimps" types...refer to my post of a month or so ago re: the Ode to my 30x27).