How do you make good trades in Rotisserie? I have one easy piece of advice that I'd put above all others. Start fair.
More than a few owners I play with or have played with don't agree with or follow this simple rule. They often start out by making a ludicrous offer that even a casual mixed league player wouldn't consider. More often than not, I don't believe that the owner making the bad offer is trying to be insulting, but rather trying to set the bar in a way that the trade works to his advantage when you do finally get past the preliminaries.
I'd rather start fair. Here's why:
I'm busy: When I was playing this game in my early 20s, I had a b.s. job, no wife, and no children. I could spend hours on the phone (that's right, when I started doing this there was no e-mail, you whippersnappers) berating someone for offering me Tim Wallach for Lee Smith.
But I don't have time for that now. A few years ago, I'd send a withering e-mail to an owner who made me a stupid offer. Now, I just ignore it and say, "no thanks." I don't know what the other owner's motivation was for making such an asinine offer but I don't care. I've got more important stuff to do than to play mind games.
Bad offers stop the conversation: Even if I’m not busy, if I get a terrible offer chances are good I’m not going to make a counter. This is because I usually don't know where to start. If someone offers me Kevin Gregg for Joakim Soria and Felix Hernandez, what's the "reasonable" counter? Do I counter with a fair offer or do make a comparably bad offer in the other direction? It's not worth it for me to figure it out, and chances are it's not worth it for my trading partners, either.
Fair leads to trades: My goal when I start trade discussions with someone is to make a trade! Yes, I want your players. To get your players, I'm probably going to have to give you something whose perceived worth is similar to what you'll give me back. We might have different ideas of what your players are worth, but if I start fair I'm going to at least wind up in the neighborhood. If I start with a poor offer, chances are we won't make a trade and I won’t improve my team…which is the goal above anything else.
Fair leads to future trades: Long-term leagues aren't just about doing well at the auction and making good trades but also about building relationships. If I offer you my garbage for your best players, why would you consider making a trade with me next time?
Owners forget this but this is perhaps one of the most important things I've learned in Roto. I've seen owners on the fence with my offer and another owner's offer take my deal because I've dealt with them fairly in the past and they just don't trust that other owner. In serious keeper leagues, never forget that there's a good chance that you'll be working with the same core of owners for years to come.
Fair leads to future trades in your favor: I make fair offers, but that doesn't mean that I never try to maximize value in a deal. Once in a while, I'll try to push for a little extra in a trade. I don't always get that little extra, but I sometimes do. My competitors are smart and might see what my edge is but since we have such a good relationship (see above) they're willing to give up the little extra on this one…knowing full well that in the spirit of fairness I might give up that little extra the next time.
Don't confuse "a little extra" with "ripping the other guy off." You still want your offer to be fair; you just might ask for a throw-in or a better player back in the deal. If you've built the relationship and have the reputation, you can do this. If your reputation is that of a jerk that makes bad offers, these trades won't happen.
In weaker leagues, you might be able to make bad offers and have someone eventually bite. Once you start playing in tougher leagues, though, the odds of this happening dwindle. I recommend starting fair. The rewards are incremental, but they are there, and yours for the taking.