1. Quite bad, though that's a mix of it seems weaker in overall talent (there'll always be variation year to year) AND it's particularly uncertain at the top.
2. Yes, #1 is relatively cheap, can either trade down or just have first overall pick, money difference isn't that big.
3. Future contract, being overly attracted to your own guys. Being overly focused on f#@*ing up and dealing with the downside is poor approach, you should focus on adapting on what you see and be willing to admit a mistake, even if it followed good process.
4 (and 5). Always debate. I think Toronto should be (is?) thinking that Barnes is a good enough player to build around, and won't want to waste his first deal rebuilding with no promise. A Quickly / RJ / Scottie / ? / Poeltl wit , Olynyk, etc should be decent though not amazing. Gets into a debate of 7 this year vs 90% having 10 next year / 9% at #10 in 2026. Small difference at 7, think you can go either way on risk preference.
6. Trade down and get more assets / Sarr / depends on the combination with the Toronto pick. You've got to think of building to a le contender eventually, and acknowledge that you're not at the point to pick for a particular need as there are so many (and, viewed with retrospect, as we're unlikely to be contending next year) BPA will be the best option. I think that's Sarr, but I don't think it's so clear where you'd take him no matter what, like Wemby was last year.
7. Mostly the same people with the Toronto pick. Maybe avoid combos like Dilly / Topic, but mostly just BPA.
8. A GOAT level player is worth about 20 wins a year, a fringe all star is probably worth about 10, with a slow progress down until 5th starters are worth 5 or so wins a year. Last year was huge (and we got lucky), this year we're looking at a tiny difference. Worst outcome is probably more Atlanta moves up (as it limits the upside of the unprotected swaps if they pick well) rather than wherever the Spurs end up. I'd love 1 and 7, but most things are fine.