Let me be clear when I say this. It isn't necessarily about the amount of the contract itself, it's the timing of paying these guys these amounts that is the issue for me unless you are getting a bargain deal or you are certain they are a max player. To me it's much more worthwhile to just let them become restricted free agents.
Take Toronto for example, I get the value of rewarding Siakam for his part in the championship. His cap hold next summer was only around $7 million but now he counts for almost $30 million against their cap and it puts them at about $80 million in contracts with only 4 players (Siakam, Lowry, Powell, and OG under contract). So instead of possibly having a max spot they will be fighting to fill their roster with a lot less money to do so.
With guys like Hield and Brown you only sign them to those particular contracts if you think they could possibly get a max contract next summer. If not you tied up cap space you didn't have to. Plus the risk of those guys getting a max offer is much smaller than the chance they could have a season not worthy of the contract they signed in which case you'd be wishing you waited to lock them up.
