What I disagree about in so many posts is that the Leafs can trade 3.5m Kerfoot for picks and then sign an equally competent centre at 1.5m. For that reason, I think Kerfoot has to stay a Leaf.
I really don't care of Hamonic even at 4m. Just keep Holl and Dermot, though it's CapFriendly thinking all other teams Dmen are so much better than the Leafs.
Don't think St Louis native Maroon comes to the Leafs. Other teams will be bid for services.

Think of it this way...

With the contracts you gave Dermott and mikheyev you have enough room to sign Demelo at 3m and keep everyone.

Less subtraction more addition. With Dermott and Mikheyev contracts here there is room to sign Demelo at 3m and keep everyone.... with a 21 man roster. Now you could also move engvall and squeeze in a 22 man roster... just to appease you lol. And realistically they probably run more than 1 healthy scratch on game nights.

I appreciate the feedback. That being said, I didn't think we were getting an equal replacement at 3rd line center I realized we were downgrading but I think we will have to make sacrifices somewhere with the cap staying flat. I thought about keeping Dermott and Holl and not signing Hamonic (or it could be any FA) and Gudas (I do like his physicality) or even signing one and keeping Kerfoot which I'm okay with too. I wanted to do an ACGM where we were signing short term contracts so we can afford to keep Rielly and give raises over the next 2 years to Hyman (I'm ok with moving on because I don't think we can afford his next contract, but our FO wants to keep him) Barabonov/Lehtonen then Sandin + Liljegren will need raises although likely bridged and Campbell plus potentially Mikheyev and Dermott.

I wasn't and don't think all other Dmen are better than the leafs I was just trying to acquire picks to hopefully add ELC's down the road (I know we wouldn't hit on all of them but hopefully a few) and replacing them with Dmen who only cost money.

I realize it's a longshot for Maroon I just like him and Gudas because they bring an element we need. I also realize it's not realistic to think we will sign 3 UFA d in one offseason.

Absolutely, I thought of a few different ways to go with this team I just wanted to see how much we could beef up our D without signing Pietrangelo as I don't think that would be a good move for us in the long term. Thanks for the input its much obliged.

This is decent.
While I like some moves, others I dont.

I'm in agreement with others on thoughts like sign DeMelo, dont sign Hamonic, dont sign Khudobin.

Keep Dermott and Holl.
I like thought of keeping Sandin in AHL needs to put on some muscle.

I want Cernak bad.

With twenty or so teams whispering about cutting costs and having internal caps, either they're all bluffing, hoping to give Pietrangelo and Hall $12M a year for life, or else maybe only five or ten teams see themselves as players in free agency this year.

Since prices are determined by supply and demand, the chance that Gudas and Hamonic each make $4M seems unlikely. Most teams either pass or take a wait and see approach.

The team is good. The blank at 3C is a little worrying. If you really only end up with 1.5M, you could move Engvall over to the middle, or trade for any of: Khaira, Lazar, Boyd, McLeod, and avoid worrying about free agency. Very different styles of players but each theoretically can play center, none seems like they get enough ice time on their current team, and they're all under 1.5M.

I'm late to this party so apologies if I'm re-hashing anything.

I'd rather keep Holl at $2m. I personally like him as a half decent 2-way D man. He seems to get better the more opportunity he gets. I remember seeing him in a pre-season game 2 years ago and being impressed at his ability to carry the puck up the ice, make a solid outlet, and stay at home when needed. Nothing spectacular, but kinda what we need.

I think Dermott and Mikheyev will get a bigger salary. It's hard to see them give $2m to Holl but less to Dermott.

Leafs will be active on Pietrangelo, Shattenkirk, Bogosian, Demelo, Gudas, etc. and they'll give Lehtonen every chance to crack the squad. I can see Sandin, Liljegren and the 1st rounder all in play to trade for a d-man, too. I could see them targeting one of the Buffalo d-men (Montour, Miller or Risto) in a trade.

I like the Freddy concept...we wouldn't need to retain as I think part of the attraction for Ottawa is using him to get to the cap floor. That being said, I'd personally rather keep him another year and lose him for nothing than get 2nd round picks for him (assuming we can fit his cap hit after addressing the D). It would be a shame to improve the back end and not see how Freddy can play behind some competency.

All in all, there's no single concept you have that doesn't make sense on some level. It's unheard of to make 5 trades and 7 UFA signings in an off-season, but as individual acquisitions I could see any one of them happening.

As others have said, there's signings I like and some that I don't like. khudobin is a product of a very good defense in front of him. Leafs are not that good and Khudobin would look horrible for this reason with the Leafs.

DeMelo vs Harmonic, I am in the sign DeMelo camp.

I'm not against signing Gudas as a second RHD as long as it's reasonable but does that mean Leafs can keep Holl for the 3rd pair? Because I'm not sold on Sandin being a 3rd pair regular. Only want to bring him up when injuries occur.

Goaltending is still the ickiest position to address because it's also the most volitile position. If there's a way to acquire a young goalie sure, otherwise Leafs may be stuck with Andersen.

I'm not to sold on Demelo. I dont think hes good enough in transition to really make in impact compared to someone like Gudas. The gap between the two is marginal imo but I could see gudas signing here for 2 million for 1 year range. They can definitely rebuild their right side without taking a huge risk in Pietro.

As of right now it looks like NYR will buy out Hank who's still been a very good goalie even at his age on a bad NYR team. If they could convince him to sign for something in the 1 million range to split time with Campbell they would be golden.

I think we're on the same page here. I think DeMelo would be good even if he isn't good enough for an expanded role but he would help. I like Gudas for his physicality and if we move out Holl and give his money to Gudas I think we would be better. Petro would screw up our cap even more than it already is IMO. Great player would love to have the player just not the contract.

Hank would make a good tandem with Campbell and I'd definitely offer him that contract just not sure if he would rather go back to Sweden at this point or continue on in the NHL. If so we definitely would be golden!