I'm calling the chessmatch a success, for several reasons.

Financially;

It raked in around $600. Half of which will be paid out to my opponents, relative to the popularity of their proposed moves.
(I've converted the SBD to steem, now just waiting 3.5 days and I'll send it out)
The other half has more than doubled my total SP, from 4000 to 8600.
I've also cracked the top 50 in the category 'Author rewards - 30 days'

Reputation.

This match has helped to propel my reputation from 55 up to 65

Followers

I've jumped from 185 to 258, a total increase of 73 followers.

Admittedly, not all of this has been from the chessmatch. I had a post hit the top of trending, which no doubt contributed to the rep and follower increases; but I'm confident this match has been and will continue to be, a source of much success on this platform.

Socialising online is less confronting, and far more convenient, than doing so IRL; but it can lack that human touch when the other party is just letters on the screen or a still photo.

That's a large part of the problem with trolling/bullying (not that we have an issue with that here); people will happily, readily say horrible things to strangers online; things they'd never say to a person's face.

I think the gifs really made the difference here.

You were playing against an actual person, somebody who waves and smiles and gives the thumbs up; somebody with a dog, and a few kids messing up the board.

The funny thing about steemit, particularly at the moment, is that we want to like each other. We're looking for reasons to be fond of other authors, because we know that its only a strong community that can really build this place and attract new people.

You take a bunch of community minded people, challenge them to collaborate against a common opponent, then bring that opponent to life, and you have a compelling experience, something that people want to be a part of.

What really struck me, was that people would occasionally suggest a dumb move, and nobody tried to make them feel stupid. These are strangers, online, messing up your game, and risking your money, but you correct them with kindness.
Can you believe that? Take a step back and think about that. Think about the calibre of people on the platform, and the incentive structure which rewards them, then compare that to literally every other site on the net.

Source

It was interesting to note that my original winner-takes-all offer was less popular than a more even distribution.
The top 3 players, @armen, @brendio and @blocktrades all agreed to split the winnings, regardless of the winner.

I struggled to make my one hour window each day, and I know others struggled to catch the post quickly, particularly when there was only one, self evident 'best' move to be suggested.
If I started the match over, I'd use ladder.net to schedule each post to be at an exact, specific time each day, and I'd close the upvoting 3 hours before hand, to give myself time to compose the post, and finalise my own move.
Draws were particularly troublesome, since I couldn't start composing my post or even be sure of my next move until an hour before it had to be posted, since a single upvote at the last minute could change everything.
I went into the match reasonably confident of a win, to be honest. I believed that the black team's inability to discreetly collude on any long term plans would scuttle them. I certainly underestimated the talent I'd be facing and the deference they'd show each other. I don't mind losing when I deserve to lose; and that was certainly the case here.
I would absolutely recommend running a similar game on this platform. It's hard work, shooting, uploading, posting, keeping track of upvotes/tallies/leaderboards, all on top of actually trying to win, but I also know that others on this platform know my name, they know my face, they'll soon know that I reliably pay out, and they like me.

The long term benefits, particularly this early in the life of steemit, are incalculable. Take a chance, and give it your all.

Feel free to advertise your game in the comments, and to make use of the #chessmatch tag if you'd like to run your own game.

And now, the match from start to finish...