I work in bulk - that is I make a TON of trades throughout the year...I try to address a particular need, even if it's a marginal gain (IMO) I take it or pursue it.
Of all the trades I make (lets say I average over 15 trades per league), I send out a ton of offers. I call them feelers...checking the temperature. I try to to make it as fair as possible but I always leave "wiggle room" on my offers in case they hit me back with a counter.
I usually like pursuing players on "the trade block" as I find guys who are posted their typically come cheaper as their GM is outright saying he is willing to move him.
I also try to compete every year. Never rebuild...I don't let "age of players" get in the way of competing (just look at my team in sig!).
I ALWAYS like to keep lines of communications open with other GMs. I'm in several leagues where I have never met the GMs in person yet I communicate with them all the time via emails or texts...I find that this is invaluable to making deals.
10-team Auction League, $160 team salary, weekly H2H, start: 6F, 4D, 1G and 5 Bench
Scoring structure: (F : 1pt G / 1pt A / 0.15pts SOG / 0.15pts Hits / 0.15pts BlkS), (G : 5 pts W / 3 pts SO / 0.01 pts Saves)
Forwards : Ovechkin ($41), Kovalchuk ($24), Kessel ($18), E. Kane ($13), Benn ($5), Sharp ($11), Pominville ($1), Dupuis ($2), Whitney ($2)
Defenses : Letang ($24), Byfuglien ($6), Markov ($1), Bogosian ($1), McDonagh ($2)
Goalies : Schneider ($7), Bobrovsky ($1)