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Do I count Battle Masters in my KO area?
Battle Masters in your KO area will be in their upgrade mode, either because they were played and subsequently left the battlefield or because you didn’t play the upgrade after the character was KO’d. This means they won’t be characters in the KO area and won’t add to Private Sideswipe’s bonus.
Source: Wave 2 and 3 FAQ
Private Sideswipe - Does his effect apply twice if you can somehow manage to get him to flip to car mode, back to bot mode to car mode again?
Yes. If you can pull it off, that would work.
Source: Rules Roundup 2019-08-09