You aren’t looking at it fromt he perspective of giving you the best chance to win a Championship. You are looking at it from the perspective of easies t and cheapest path. The cheapest/easiest path is rarely the winner.
IMO, Oshawa needs a repalcement for the role Punnett played last year. They also need a 2C to take advantage of their top end forward talent.
If it is strictly a draft pick trade, Romani will likely cost a 2nd, 3rd, and 4th more than Wakely. You can use the Rehkopf and Morrison deals as the comparables. That likely makes it more difficult to get the D-Man you need without giving more players and less draft picks.
Oshawa has four 2nds, four 3rds, and five 4ths. It is likely they get Walkely for two 2nds, two 3rds, and two 4ths. That aligns with the Morrison deal. Then they can add the same picks package and one young player for a key D-Man like Amidovski or Gibson. After that, the Gens are done with respect to covering off key positions (assuming Roobroeck returns).