Here's how I compared both packages (in order of value IMO) :
1) 2018 1st round pick (TOR) 25th OA vs 2019 OR 2020 1st round pick (SJ) : I prefer the odds of that SJ pick, particularly in 2020 if they miss the playoffs. Or even this year if they miss the playoffs, could be in the lotto. Sens could hit a homerun with that pick, even if it doesn't end that high (see Karlsson, Chabot, etc)
2) Jeremy Bracco vs Rudolf Balcers : Both players are the same age. Balcers just had a very impressive rookie season in the AHL, he was ranked Sharks 2nd best prospect after Merkley. Bracco played on a much better AHL team, Balcers lead his team in scoring as a rookie by 10 pts...
3) Andreas Borgman vs Josh Norris : taking the 2017 19th OA pick here, not even close
4) Josh Leivo vs Chris Tierney : Leivo is 1 year older and still doesn't have a full NHL season under his belt. Tierney has 3... Plus, Tierney looks like he could have some impact
5) 2018 2nd round pick (TOR) 56th OA vs 2019 2nd round pick (highest between SJ/Florida) : I prefer the odds of that Panthers/Sharks pick.
6) Calvin Pickard vs Dylan DeMelo : DeMelo might just be a 3rd pairing D-man and he was the least valuable piece in the Sharks return, but Pickard didn't have any trade value, he got claimed on waivers recently
n/a) 2019 2nd round pick (TOR) vs conditionals : impossible to tell right now but there's 2 conditions where the Sens could end up with another 1st
Also, retaining Ryan at 50% to trade him doesn't accomplish much. He is still a capable forward, just way overpaid. People wouldn't complain as much if he was making like before 5.1 per year. He had monster playoffs in 2017 and despite another injury plagued season, he had a 0.53 PPG last year. If the Sens were to trade him while retaining 3 575 000$, they would also have to find a replacement who can produce ~0.50 PPG, so even if that guy makes 1.0 per year, it costs you ~4.5 per season to "get rid" of Ryan" and have similar production.
