With checkpoint style, do you mean one has to stand around the flag to capture it for some time? Or is it just touch and done?
For the later there is already a map having that, alleys
http://activegamer.net/et/map/295-Alleys_(Final).html
Then in any case, the scoreboard is useful if it depends how many got captured - but location does not matter.
So maybe instead of a scoreboard, have the command map updated with what is captured, and I thought about having a display, maybe the radar reticle could show those 8 flags, so one has more or less an idea which one got captured - although I guess that is not really helping. Well maybe after a few times one knows - which flag on the reticle is which on the map…
Having played the map alleys a few times, I can tell that it is very hard, one has no idea which flag is captured - chat is full of spam.
And if one team has a few objective players and the other not, the flags get capture in no time.
As such I thought it would be nice, if it needs an engineer or maybe a covert ops, to destroy a flag, and to capture it one has to build it.
This would also give the engineer class something todo.

After playing it ofc 