Realistic next year

Don't sign Simmonds, don't trade for Crouse, carry 20 skaters and keep kerfoot who is better than Staal at this point

A team in a cap crunch shouldn't be paying over 1 mil for fourth liners

Don't hate this, though I don't really see Staal as an option for the team. Keefe has been saying pretty much since the day he took over that he wants a 3rd line as a shutdown line and Staal isn't really a fit for that. I think Riley Nash will impress enough to be brought back and centre the shutdown line, Keefe said he's liked him since he saw him in the bubble so I think he'll impress him now.

I do like the top 6 though! I think Robertson has been the answer all along and they're just waiting for him to be ready for more minutes. And Galch has look even better on the top line than he did with Tavares and Nylander so the fit is there.

I think Bogosian will play himself out of Toronto. He hasn't been great this season but he hasn't been bad. I just think he'll be looking for a bigger raise this off-season and won't be able to fit in Toronto, although I think they highly consider bringing him back.

A lot of this obviously depends on the expansion draft and Kerfoot being taken for salary relief. I assume you protected the 8-1 option? Which would leave Kerfoot and Dermott available. I think Seattle wold take Kerfoot too, but if I'm Dubas then I'm throwing something at Ron Francis to make sure he takes Kerfoot so I knew I had the money to re-sign Hyman and not have to worry about leaving him exposed as a pending UFA.

Goaltending is a big question mark to me here. I'm not a big believer in Rittich and I don't think he deserves his same salary after a poor last 2 seasons. Campbell seems too injury prone to be ready for a starter's role so I'd bring in someone that could handle a bigger load if needed. What would your thoughts be on bringing Andersen back on a cheap 1 year deal to prove it again? I think as rough of a year as its been for him it may work out well for Toronto because now they can bring him back cheaper, and see who's really better between him and Campbell.

I actually just posted something pretty similar to what you have here with a lot of the things from my comment here. Check it out if you wanna see more of a visual of what I was thinking:

https://www.capfriendly.com/forums/thread/440574?post_id=2266659

I do like the Crouse deal.

Kerfoot is likely Seattle bound (provided the leafs protect Holl and go 4-4)
So, to replace his depth scoring, you need more options. Based on the deadline, the leafs have no problem is paying 4th liners over 1 mil now, and there's no reason they should. And the leafs have realized grit is essentual to success as a team. Simmonds and Crouse provide that. I don't deny Kerfoot is better than Staal. But Staal is cheaper. Also it doesn't have to be Staal, it can be another veteran guy for a similar price, for example, Nash or Goodrow (I think he's a centre...).