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When initiating a trade are you supposed to trade in the other person favor, or does it matter?   I usually try to trade in the other persons favor when I initiate a trade if possible.  But lately it’s been the other way around.  People initiating the trade are asking for way too much in return for next to nothing.   

I agree that in the last few years, this is happening more and more often. That comes with the increased membership. From these you will hear all sorts of justification - B******* value, price on site, etc.  When I see something way out of whack, I simply decline. If it is something I can work with, I counter with a message explaining my reasoning.

Using the Decline option more frequently will help these types either leave the site or be more reasonable in future trade offers.

Just reply "Respectfully Decline"

In my attempts to remain a glass half full person - going on about 20 years of that - I am finding it hard to match valuations with many traders, and not necessarily newbies. My trading has slowed considerably to what it once was.

Proposing a trade in the others persons favor was my approach. I don't think I have ever received the same sort of balance when receiving trades. For the most part people want hard to find items for nothing cards at a ratio of 1 for 1. This led me to turn off trades since 90% were not even close to reality.

I agree with others that a rejection is easy enough to do to save oneself from the hassle.

I will say that if an offer seems off, I tend to look at the feedback numbers as well as longevity on the site. If someone like sandyrusty or Sportzcommish sent me an offer that seemed off, not only would I probably think they have thought about their valuations but I would also like to think they'd be open to a discussion. If the person offering you something doesn't have much history here, or has an aggressive/flippant tone, it's probably not worth the mental cycles to try to come up with something that works. 

I enjoy trading and try to make something work, but there are plenty of traders here who aren't trying to rip people off, so I try to focus on them.

When I first joined, a lot of the offers I made were an attempt to match value or to "win" the trade slightly in my advantage. 

Nowadays the offers I make are attempts to get stuff out of my hands and into someone who wants them. I've found that tipping the scales (quantity and/or value) helps entice people's desire to transact with me.

All that being said, every trade is it's own thing and sometimes I get offers or counters that make me think "not a chance" and I won't bother negotiating. 

Value of cards is very subjective to begin with.  What one person might see as a fair trade, another might see as being off.  I know I've made trade offers that I thought were fair that got rejections with a comment from the other saying they didn't see them as fair, and I've been on the other side, receiving offers like that as well.  I've also taken a few offers that I knew were imbalanced for the other person because they had a card I really wanted.  Even though the "value" was off, I still saw it as fair.

Of course, there are also those who will send crazy trade offers of something like a 1990 Donruss common for a Henderson Topps Rookie or something way off like that.  Trade offers like that leave me wondering if the person was serious or what they were thinking.  Even someone completely new to the site should know better on something like that.

As always, I scan profile/feedback to attempt to get a better picture. If I see a lot of "Value" and "Mint/NM" stuff, I am fairly sure there has been some work done on their end determining what they see as a fair trade. Then it's up to me to decide; my decision that I need to live with. I generally decline those offers as condition and worth aren't my priorities. As far as me proposing, I try to weigh it in the other end's favor out of respect.

I typically approach it trying to send what I think is a fair/balanced trade or tipped a little in the other person's favor. Of course "fair" is subjective as has been stated already in this thread. I once sent what I thought was a fair trade and got a response back that it was the worst trade the user had ever seen so I obviously haven't tried to trade with that person again since we obviously value things differently.