Leafs are cap compliant without a trade. Reports are there is a significant market if dubas wants to move him too. You're gonna have to pay up if you want him

83+ million team cap hit without sandin signed, last I checked 83 is bigger than 82.5

If Toronto sends both Clifford and Simmonds down, trade Holl for whatever (probably for a 4th or 5th, maybe 3rd if were really really lucky) and sign Sandin for the same amount that Liljegren signed for ($1.4M) we would have a 21 man roster with 20k to spare.

Now that's not really realistic since Sandin wants more and playing with a 21 man roster with only 20k is playing with fire. However, the point is that Toronto would be able to make it work. If we look at Columbus they needed to offload at least 5M to become cap compliant so they desperately needed to trade Bjorkstrand that's why the return was so bad. So, the point is that Dubas is just waiting for a team to bit to get the best possible offer and if there is a market we could end up getting more than Bjorkstrand so a 2nd or more. If not than we probably will get a little less like a 3rd.

CF doesn't show final rosters since they obv don't know who's all made the team yet. Leafs simply send guys down and it (just) works.
Point is, You're gonna need a late 1st of value coming back. That probably looks like a 2nd and a B. I'm using a slightly outdated prospecting list from 6 months ago but I like Rory Kerins (ranked 8th in your list). Soo guy too so it makes sense.

Kerf for 2023 2nd and Kerins seems about right

You're dreaming. Kerfoot and his contract is worth about zero. 2025 3rd is slightly better than that so its a fine proposal.

maybe make it a 2024 and the leafs say yes

I've seen some wild things here before, but suggesting holl may net the Leafs a third is laughable