What I’m trying to do:
Sidebars on the outside margins of pages.
Sidebars will contain multiple block-quotes that are usually less than a page long, but not always.
Here's the extent of what I've done so far:
needHelp.pdf‎

Constraints on how I'd like the block-quotes to split between pages: :

• Don’t split the block-quotes between pages unless the block is longer than a page.
• If longer than a page begin block at the top its page.

Problems I’m having:

• The block-quotes sometimes overlap, with one beginning before another ends.
• In an attempt to layout the block-quotes correctly, the layout engine is shifting paragraphs of core book text to new pages needlessly.
• I’d like to get page numbers all the way out to the actual corners of the page (above the outside margins).

My experience level:
I’ve been learning just enough css to layout my book. I usually hack things together and if they work, I move on with a feeling of confidence that only ignorance can achieve. I have done other kinds of programming though so I’m not totally lost, and will usually be able to solve my problems if someone points me in the right direction.

I have two options right now. I can either proceed with the sidebar layout, or give up and put all the block-quotes into their own chapter. If the sidebar layout is going to be a headache, I’m willing to take the other option.

My Questions:

• Is what I’m trying to do in my sidebars is really do-able, given my constraints?
• If do-able, is it difficult, or easy?
• If it’s easy would someone be kind enough to point me in the right direction with regard to the necessary css? I've found a smattering of discussions on sidebars in the forum but none that really seem to solve my problems. If I've missed something let me know.

@media print
{
	blockquote.humor
	{
		float: outside;
		clear:outside;
		margin-outside: -5cm;
		width:3.7cm;
		margin-left:0;
		margin-right:0;
		background-color:white;
		border-style:none;
		
		page-break-inside:avoid;
	}
}

1. needHelp.pdf‎ 147.7 kB

I'm confident that this isn't easy, given the constraints that you've listed. Ideally it would be possible, but some investigation will be needed in order to confirm or deny that. So I would suggest investigating alternative arrangements, in the meantime.

Thanks for saving me a lot of frustration.
Much appreciated!