Can money be saved by NOT ordering when they're for sale on standard edition busts? For example, I just got Maul for $35 and Vader for $39 - are edition size and exclusiveness enough to know whether or not one will cost more than or less than $50 later on?
Yes, this is my strategy for ordering busts now. If it's a regular release bust with an edition size of 10,000 or more, no way am I ordering it in advance. I did this with Vader (paid under $20 pre-shipping for it) and Yoda (OT version - paid $22 or so pre-shipping cost) while both listed at $50 MSRP. Maul is similar, though he is proving tougher to find for under $30 before shipping. I've been quite surprised by it to be honest, I thought it would be more readily available at lower prices though the edition size is smaller than Vader/Yoda. The Stormtrooper is another oddity, owing I think to the multiple poses and some folks wanting more than one. It was a large issue and it's price is usually above retail these days.
In the mid range of edition sizes is where I get stuck: 4000-7500. I'm never sure what to do with these. The sandtrooper busts would be a good example. I paid only $39 for each on a pre-order (and you can still get them at online retailers for that price) but could have actually picked up each for less than that, just a shade over $30. Is that worth the grief of sweating and watching ebay? Probably not, so generally I tend to buy these in advance. I know Nicklab goes through his local comic store, via Diamond Dist. I think. I generally order from Talesofwonder.com as their prices are really good usually on pre-order (Leia/Ben are $39) and others go through BBTS or Newforce. If you miss these, they tend to stay at or around retail for a pretty long time. One of the first busts I picked up, the Biker Scout, was sold out at retailers yet I still picked it up for under $40 on ebay. It's finally creeping up though and going over retail now regularly.
Low edition sizes are almost always a crap shoot and it depends as much on the character as anything else. Show exclusives seem to settle out in the $90-150 range after the initial rush dies out. Mara Jade and the Shocktrooper bust from last year seem to fit that pattern and I've seen both go for under $100 lately.
I think it best to try and hook up with someone at the show if they can help you out, but I try to be realistic about them standing in a line for me. I know what it was like at C3, so I imagine it's not that different at SDCC or the like. For me, show exlusive busts are reasonable at $100 or so because I didn't have to pay admission to the show, which probably would run $50 anyway.
Super low edition sizes of 1000 or less are just a huge pain in the ass and it's a crapshoot to get one. I've been really fortunate of late, but I'm not even contemplating getting any of the early (red/white/yellow/blue) AOTC clone busts simply because they run too rich for my blood. I could probably get the white and yellow (both of which have edition sizes above 1000 btw) and not feel too bad, but I'm not dropping $400++ on the red or blue any time soon. And with such small sizes, the probability of someone selling one to you cheap is very low.
Going backwards to fill holes? Ick, I don't envy you. Ebay is about it unless you can come across someone getting out. Even then, it's doubtful they'll just be looking for retail. I would check what you can online for some of the busts as they may still be available, but that's unlikely for most.
As for the premiere membership with GG, it sounds as though the really rare stuff is going to be run as a lottery for the premiere members. With only 500 of whatever it is usually available and 500+ members, they'll let you submit your name and then luck (maybe, maybe not) will determine if you're getting the exclusive you've entered in for. I'm not sure if I like that better than the usual jam-up-the-server with a first come, first served approach but it seems to be the direction they're going. So the $50 may or may not have any benefit, though it looks like we're getting that Chewie with Mynock Mask for our $$. I don't know if it's an outright gift, or if the $50 entitles us to buy the darn thing. Mine will be up for trade for one of the commander busts though

Otherwise it looks to be as though the lottery will be the way.