These are SO much better looking than the designs you currently have up on the KS page.
After a crazy weekend of scrambling that is really encouraging to hear, thanks! 
We don't want to overwhelm the kickstarter crowd with too many choices, so I'm hoping to pare it down to 2 or 3 options based on feedback from the forums. Would you prefer two color variations on the same design, or two different designs? Which ones do you like best with the ammo can theme?
First, welcome to the forums, Sam. Glad to have you on board.
You mentioned concerns about the quality of the chips. FORGET those concerns. The chips are a fine "home poker kit" grade - they're just not the "casino grade" you were advertising - just be honest about that and you're good to go. Rather than going crazy looking for a new set of better chips to offer as an upgrade, offer a cheaper tier with NO chips, for those players wishing to source their own. The thing I would do, however, is look into the cost of upgrading those chips to have a custom logo on them, something matching to the set. Choosing chip colors to go with the decks and the box is also worth considering.
The new deck backs look excellent - but I would veto the Generalissimo. From an accuracy standpoint, you're displaying a five-star rank (which no longer exists) with a modified staff sergeant's rank. Not too big of a deal unless you're a stickler for military rank. The bigger concern is how the inclusion of the pips in each set of sergeant's stripes makes the back into a one-way design - a serious no-no for cards meant for use at a poker table. The needs for a poker deck are very specific, and two-way backs is chief among them.
The back I like the most is the Honor Guard. It's simple, it's classic, it doesn't have a seemingly-generic pattern in the background, and it has a thin, white border. If you want a background design, create something unique rather than use something that looks like it was taken from clip art. Conversely, if you still want a simple pattern, go VERY simple - geometric rather than clip art (stars and/or stripes would be good for a deck like this, very small and subtle). And did I neglect to mention that Honor Guard shares certain design elements in common with two popular poker card backs, the Bicycle Rider Back and the Tally Ho Original Circle Back?
A black border isn't good for a poker set - poker players are very hard on their cards, so the black will begin to chip at the edges and the cards will look like crap in a single night. (That happens with any color besides white, since USPC always starts with white paper - the darker the color, the more noticeable the effect becomes.) The best choices are either a white border, or a simple, repetitive pattern that's printed into the bleed - most classic playing card designs have one of these features. The patterned back (a la the Bee DIamond Back) is a popular design - but also bear in mind that some poker players will shy away from them - the back can create an illusory pattern when the cards are handled and spread, making it difficult to tell where one card ends and the next begins, thus allowing a card cheat to better conceal some of his sleight-of-hand work.
Yes, you would want two of the same back in differing colors - red and blue are traditional, though you could use green, black or brown to swap for one or both of those colors easily enough. Keep the colors a little dark and easily distinguished from each other - I still remember when USPC released a special Kem set for the World Poker Tour that had two differently-colored decks: light black and dark gray! Needless to say, it was not a popular set among players.
I wouldn't go too crazy with the customization level, assuming you're targeting poker players. Even the casual poker player at a neighborhood game likes his cards to be simple and easy to read in a hurry - a custom design mentally slows that process down just a little. Furthermore, any custom design for a set meant for poker would have to have some of the traditional court elements that are popular in neighborhood games, like "the man with the ax" on the King of Diamonds, the "suicide king" on the King of Hearts, the "Bedpost Queen" on the Queen of Spades, and all the assorted weapons, flowers, crowns, profile faces, etc. - you'd want them all to match the Anglo-American standard. A strong custom Ace of Spades and pair of Jokers is enough.
A nice additional touch, though, would be a recoloring of the cards in the traditional designs. Casinos often use a much darker shade of red on their cards than the off-the-rack packs from the local pharmacy - it shows up better on video surveillance cameras, especially back in the days when they were mostly black-and-white. You also have some flexibility in playing with the palette used on the courts, as well - again, make colors that match your poker kit and players will enjoy them. (AND PLEASE - make the faces IDENTICAL for both decks!)
The one innovation I would even consider is a change to the background color. White can be a little hard on the eyes over time - it's why legal pads come in yellow more often than not. Consider a pale shade of yellow, taupe, gray - something leaning toward neutral - that would be just enough to take the edge off the glare without being a full-blown color change. A light shade will conceal edge chipping better than a darker one. so there's that, as well.
That should give you enough to chew on for now. If I can think of anything else, I'll let you know!
