Wyatt pretty consistently said that Tom fired from behind the horse (over its back or under its neck), so we can pretty well conclude that Wyatt said that.
You can see similar patterns in other things in the 1896 articles. Research involves comparisons between various statements made. I wouldn't even argue that Chandler deliberately misrepresented what Wyatt told him. What he did do was write in a manner that Wyatt would not have (Wyatt was no writer), and that, in telling the story, Chandler may have added a detail or two or even misunderstood what Wyatt said. He didn't have a tape recorder. What he wrote had to be based on notes. As someone who has taken notes in interviews before, I know that sometimes in reviewing notes it is possible to cross a line between what the other person said and what I thought when he said it.
Why stupid? Earp had experience with Wells, Fargo. If he sent a simple note asking if the reward would be paid dead or alive that would be simply a general information type telegram as far as anybody else was concerned. There would be no reason for Marshall Williams to suspect a "deal" with anyone, and certainly not a deal with Ike Clanton specifically. It would have been even more suspicious to have gone to Benson or Tucson. What information did Williams have? He had information that the reward would be paid dead or alive. Something else had to happen for him to put two and two together. He may have been suspicious, but we have no real understanding of why. The open telegram and Rowell's response did not mention Ike or anybody else. What was supposed to be a "secret" quickly got out of hand with Joe Hill, Frank McLaury, Virgil Earp, and possibly more aware of what had been proposed, any of that bunch, including Wyatt and Ike, could have had a slip of the tongue.
Back to your original point, if you have more than one account attributed to an individual, comparison is one of your best tools. But, with that said, we still have to be cautious. Sometimes people misremember. Sometimes we state something as a fact from our memory which may be something we heard from someone else or that we read somewhere. Sometimes we get confused. Sometimes we tell what we think happened rather than what we know happened. What we believe can easily become a "fact" in our memory.
There are many factors that can affect a reminiscence. Is the account selective (Does the writer deliberately leave things out and pick and choose what he includes)? What are the psychological needs of the writer? Is he a pessimist or an optimist? To what extent is the writer attempting to shade the story and why? What prejudices affect an account? What outside influences affect the account? Was the person in a position to know what he claims to know? For example, some things in any recollection are about what he actually saw, but other things (that fill out the story) are about things of which he had no direct knowledge. When Breakenridge wrote about the street fight, for example, he was writing about something he had no first hand knowledge of; he was not there. The same can be said of Wyatt's recollections as well. Who is the audience for the reminiscence? Is this an on-the-fly interview with a reporter for which the interviewed person has not prepared himself? Or is it a part of a calculated effort by an individual who is taking great care to remember correctly and/or to show himself in the best possible light? What role does vanity play? Does the person telling the story feel the need to "set the record straight," which means that he wants to correct the errors he believes have been told about him and the events he's been part of?
Some of these things may be pretty obvious, but they are not always obvious, in which cases you have to put accounts into boxes, adding to them with other accounts, weighing the credibility of the sources taken together, and reevaluating as you acquire new materials. Don't look for the answers to be obvious.
Best!