I do remote network, so I can answer some of this.
Number 1 = No. ESPN is aware their streaming service sucks, but it's not for the reason you think; and it's proven by the "commercials work, but live stream doesn't". It's not a lack of resources.
ESPN has been, for a few years now, testing what's called a REMI show. This is where, instead of showing up with [at least] two 53 foot production trucks (A/B units) they show up with what's basically a minivan or just an A unit. The cameras get hooked to said unit, and then everything is sent to Bristol where there's a stationary director/td/etc.etc. that does multi shows a day. This saves ESPN a whole lot of money but it's been causing havoc since it was implemented. These days there's basically half Remi so the TV at least gets a good feed but it's a major cluster fuck.
The internet feed, because of said commercials, is transmitted separately. The TV feed is split up by area so the appropriate commercials can air (you don't want Los Angeles Ford Dealer being advertised in Texas). The internet commercials work because they're starting in Bristol and being broadcast out from AVS (video storage on a computer). On site we still do camera to lunchbox to SMPTE or fiber to ipv4 switch to internet. Why the hell we use ipv4 is still puzzling but we do which makes this even harder to pull off.
Basically... Yeah, we know about the problems. We (the lower level people) even know what the hell causes it. But the execs and board just want to save a penny at any cost. They don't know what to do anymore as we are losing revenue. Before the average cable subscriber paid $7/month to ESPN. We were the highest fee cable channel, I think the next highest was a buck something. We used to have money coming out our asses, it was ridiculous. The remote people like myself blew money like no tomorrow and no one cared. These days, it's penny pinching because we went from what was effectively unlimited money to not a lot of money for what goes on.
If you think this is getting fixed anytime soon, think again. You can bitch, everyone can bitch, the employees can bitch, it's not going to fix the problem as no ones going to budget a fix. Internally ESPN is a massive cluster fuck right now.
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