Understand, if you will, that I still have relatively close access to two LHBSs, and I want to help keep them in business.
If I have to go internet order, I'll give you first shot.
The "good" news -- commercial beers are increasing along with everything else, so we retain an economic advantage in brewing our own, and that doesn't even take into account the positive impacts on our lives of having a hobby that not only keeps you busy, but results in delicious consumables!
Plus three weeks in the fermenter leaves most of the sediment on the bottom. Siphon/drain from above the sediment line and you should have fairly clear beer.
Let the bag drain over the pot, and squeeze/twist it if you have to. If you're not getting as much gravity as you're expecting, you might be leaving quarts of good sweetness in the bag...
Sorry this is so late. Two ways -- get some heavy duty rubber gloves and squeeze the bag like it owes you money. Or you can literally twist it round-and-round while holding the top of the bag steady, and the constriction will squeeze down on the grain.
If you can get them, a 24-pack case of Samuel Adams (any variety) will go a long way towards satisfying your bottling needs. Labels come off with a good hot soak and minor scraping with a razor blade. Keep the case (reinforced with packing tape) or get the square plastic milk crates at Target...
I would imagine most people never get close to 200 gals per year. But based on some of the totals in the annual output thread, there are certainly some who do.