Well, I can't help you with all your questions, but I may be able to answer a few.
First, when on eBay, I always set it to "Buy it Now" and "Newly Listed" and then if there is a really good deal you can get it before others even see it! Personally, I would try craigslist and garage sales near you (though it's pretty late in the year for garage sales). Maybe put an ad in the paper or craigslist, "looking for LEGO" or something (but make it catchy). I've had some good luck with asking nearly everyone I know if they have any LEGO they don't use anymore, especially high school graduates going off to collage, a lot of them keep their LEGO but when they move they just don't want it anymore.
Rocao at brickset just said this the other day:
I'd start at a $10/lb valuation for a good condition, unpilfered (minifigs, baseplates, or other desirable parts not removed) collection.
As the condition or the specificity of parts worsened, so too did my valuation.
That seems about right for some stuff I've bought, but is usually harder to find online.
Maybe try a search more like this (scroll down about halfway and then you'll see more) if you're looking for it by the pound or a better feel for what people are selling LEGO lots for:
http://www.ebay.com/sch/i.html?LH_BIN=1
mp;_sop=15
Also, look if they have things kind of sorted or not. So many people say New Mint LEGO or All LEGO bricks or ONLY LEGO toys, etc. and a lot of the time I see things that aren't LEGO in their listings! So (I know this probably isn't exactly what you're looking for, but who knows) if you see they care about LEGO it's probably better, like this:
http://www.ebay.com/itm/HUGE-LOT-OF-OVE
3f1fa39799
Is way more likely to have only LEGO and good quality pieces than, say, this:
http://www.ebay.com/itm/Huge-LEGO-130-L
4d076f3f28
With all the stuff in a big mess, just thrown in the bins, minifigs missing hands or drawn on, etc.
I'm not sure how helpful any of this is but I hope I've given you some basic ideas.
JonnDthunDer