Depends on how realistic you want it to be. Trade logic isn't great, so if you're not into realism, then I would start by shedding your bad contracts. Even when you turn trade difficulty in your franchise to hard, you can still spam other GM's into taking on bad contracts. 3rd and 4th round picks are like gold in this game when it comes to swaying opposing GM's into accepting trades. Grab them when you get the chance.
I like to keep it realistic, so unless it's a Clarkson for Horton (bad contract for bad contract) type trade, I won't make it. I traded for Duchene in my Expansion franchise, and tried to match up with Sakic's real life asking price (NHL ready Dman, top prospect, 1st rounder) as close as a could, but subbed 2 2nd's in instead, since, as an expansion team, the value of my first is huge.
When it comes to resigning players in the offseason, I release any RFA or UFA player that has a potential below 7th defenseman, bottom 6 fwd, or backup goalie. Doesn't make sense to resign them when you can just slightly overpay a few low overall/high potential FA's when July 1st hits.
Scouting is kind of a crap shoot. It sucks that you can only scout one position in one region at a time. I usually just pin a few top guys that I'm interested in drafting, and then let the CPU scout for me.
Hope this helps...if you've got any other questions, feel free to PM me!