This NBA Trade Machine is a fun software. I wish you could add the 1st, 2nd round picks directly into it, but its really more focused on just seeing if the trades would work salary cap wise.
I think the first trade you came up with
Cavaliers Receive: Harkless, Aminu, Ed Davis, Zach Collins, 2018 1st Rd Pick, Lottery Protected 2019 1st Rd Pick For Kevin Love, Kyle Korver, Ante Zizic is the best.
The Blazers should be willing to give up something extra for Kevin Love being a home grown kid but I actually think they would be giving up to much. Even without the extra First Round Pick, Cavs should be happy to get those 4 young players.
***The real implosion happened before the season even began. Cavs should have pulled a Jerry West, picked the younger Kyrie over Lebron, i.e Shaq & Kobe. I hope Kyrie continues to stick it to these guys for many years to come. He was really torn apart for a good month after his decision, looks like he can laugh at that now.
I don't think there's any way the Cavs can let Kevin Love go without getting at least one 1st Rd Pick. Love is a great stretch-4 and one of the more efficient scorers in the NBA. He's well deserving of a 1st for sure.