I found in the past that where there's a will, there's usually a way. I have no inside connections but have never been shutout. I don't always get fantastic seats, etc but I usually make out ok. If you go to enough shows, you also start to learn tricks to getting tickets (like the pre-sales and pre pre-sales these days help a lot if you get the codes)
That being said, I agree with many of your comments. I met the Lady with a fan and husband on the East Coast a couple of times. They seemed nice enough when conversing with them, but I also got the we know people, we're special vibe from them. They always seemed to have good tickets, way to often to be doing it on their own (the disclaimer is that I don't really know them so I am just reflecting what I perceived from talking to them). I suspect a large number of the people who got into the Sweetwater (and TXR shows) got in via some connection with the band or friends of the band. In fact, when I see people complaining about the ticket costs for these venues, I don't think they are realistic when they multiply the number of potential tickets times the cost as I suspect a chunk of tickets are complimentary. I would guess that the number of tickets available via the lottery was modest. I think this is just the way life works. People with connections, people with money, etc often make out. And to be fair, I could see giving people who support the shows at TXR and Sweetwater in general or are local a little help in getting into these shows.
The 'push their way in at the last second' and aggressive crowd bothers me more than the other stuff. I go to shows alone usually because most of my friends gave up after Jerry died. I routinely have negative experiences at GA shows with aggressive people who come in at the last second, stand in front of me, crowd me out, etc.
In the case of the Sweetwater shows, however, I have a hard time complaining. The streams were awesome as were the shows!