I agree with you on some of your points, and likely dislike the "Yuppies" you bring up as much as Bill "Die Yuppie Scum" Gleason from the Daily Southtown Economist on the Sports Writers on TV back in the day.
In terms of the White Sox, their fan base are by and large historically working / middle class fans with families from the South, West and Near West Sides. Cubs gathered a lot of transplants, a good portion being college grads moving here after perhaps watching Harry and the Cubs for decades. Harry left the Sox because he wanted to reach all Chicagoans including those who couldn't afford Sportsvision/PPV/On-TV. We didn't even get a color TV until I believe a hand me down one in the late 70s or early 80s.
In terms of Vegas, Paradise isn't a suburb, but more similar to unincorporated Cook County. Casinos built the Strip (south of Sahara) to avoid taxes paid to downtown Vegas, but the city and Clark County provide all government services (schools, police, water, etc.). Their original parcel was on the site of the trucker prostitute hotel/casino, Station Casinos owned Wild Wild West, which offered enough land to engage in these real estate developments you not in your post. I believe Days Inn managed the hotels before they ended up shutting down the site.
However, the Stadium bill was not going to pass with the Culinary Union blocking it (the WWW site is owned by non-union Stations Casinos, whereas unions have deals with the Tropicana Hotel and most other Vegas casinos. So the legislature passed the revised bill, and the A's total land purchase shrunk from the WWW 49 acres (with an additional option to purchase more adjacent land) to the current 35 acres on The Strip.
So there is still room for some development, but not to the extent the A's could have gotten at the Wild Wild West Site, and a small fraction of what they would have gotten with more capital up front at the Howard Terminal Proposal (stadium + 3,000 residential units plus 1.5 million square feet of commercial space + an indoor performance theater, a hotel with 400 rooms and 18 acres of open space.
The A's bitched about the funding for the infrastructure and the portion of affordable housing subsidies for Howard Terminal, but got everything else they wanted, and ended up walking away from the much larger real estate play than what they ended up with in Las Vegas, all for the portion of the $352M of infrastructure the A's.
So bottom line, their real estate footprint beyond the stadium is much smaller in Vegas, their television revenue will be smaller than their previous years, and while they will likely be able to charge a higher ticket cost per seat and get substantial skybox suite support from casinos, they will have trouble drawing over 2M after perhaps the first year or two between the location and small capacity, whereas they would have made a lot more overall revenue and capital appreciation at the Howard Terminal. I believe Fischer thought they would be able to get everything they wanted in Nevada, but after the Raiders experience, they didn't get nearly as much as they thought they would.
I feel bad for Vegas getting Fischer after already being stuck with Mark Davis and his roster of seemingly weekly DUI players. I hope Oakland (or Montreal) gets one or both MLB expansion teams. I'm still not sold on the long term prospects in Nashville between the weather, culture, size of market and other factors, but I believe in the end it will be Nashville and Oakland approved, as Manfred is like Bettman in terms of hating Canada because they don't build stadiums for billionaires with taxpayer funds (well unless they get a hand-me-down Olympic Stadium). I have to laugh at Salt Lake City, Portland and Orlando being listed.
https://www.si.com/mlb/athletics/news/oakland-reportedly-a-top-two-expansion-site-if-as-leave-for-las-vegas