Once the game begins, your two commanders are tracked separately. If you cast one, you won’t have to pay an additional {2} the first time you cast the other. A player loses the game after having been dealt 21 combat damage from any one of them, not from both of them combined (although your Background won’t usually be a creature anyway).

Both commanders start in the command zone, and the remaining 98 cards (or 58 cards in a Commander Draft game) of your deck are shuffled to become your library.

The copy effect doesn't have a duration. It lasts until the commander leaves the battlefield, though another copy effect with a later timestamp (perhaps from a new activation of the ability granted by Shameless Charlatan) would override the effect for as long as it's active.

Choose a Background is a variant of the partner ability. You may have two commanders if one of them is a legendary creature with the choose a background ability and the other is a legendary Background enchantment. Backgrounds and cards with choose a Background do not interact with cards which have any other partner ability.

If you control a Background that grants an ability to commander creatures you own, and you own more than one commander creature, each of them will have that ability.

If Shameless Charlatan is your commander and somehow becomes a creature, and you use the ability it grants itself to make it a copy of another creature, it will no longer have its ability so it would no longer grant the activated ability to commander creatures you own (including itself).

You can choose two commanders that are the same color or colors.

If a card refers to a commander creature you own, a Background won't usually be counted or included for that effect. If another spell or ability causes your Background to become a creature, however, it will be included. Any effect that refers to your commander or a commander you own or control without specifying creature will apply to a Background that is your commander, as appropriate.

If your commander loses the choose a Background ability or stops being a Background during the game, as appropriate, it is still your commander.

If something refers to your commander while you have two commanders, it refers to one of them of your choice. If you are instructed to perform an action on your commander (e.g. put it from the command zone into your hand due to Command Beacon), you choose one of your commanders at the time the effect happens.

An effect that checks whether you control your commander is satisfied if you control one or both of your two commanders.

If your commander becomes a copy of something else while you control Shameless Charlatan, it will still be your commander and it will still have the ability granted to it.

If your Commander deck has two commanders, you can include only cards whose own color identities are also found in your commanders’ combined color identities.