OK, now that I've played this, my main beef with it is the same one I have with most KOTH maps that have multiple control points: The "timers" count down at a variable rate, making them not actually timers at all. At least in those maps, it's not too bad because either one timer is paused or they're both counting down at the same rate, so at least it's clear who will win if no further captures are made before the round ends. Here, it's much worse because you can have both timers counting down at varying rates, so one team can have more time left on their clock but end up losing anyway, and the only hint that they will is that they have fewer points. Not that it matters much, because the points can change ownership so fast and so often that knowing who will win if no further captures are made is practically useless information.
(Does this make sense so far? I feel like I'm not explaining it well.)
I don't know what could be done about the latter issue, but as far as conveying information goes, I'd recommend changing the timer logic so that instead of counting down at different rates, capturing a point either adds time to the team's clock or subtracts it from the other team's. Or both. I was going to suggest having it actually calculate how much time would be left until it reached zero if the rates were adjusted, and then instead adjust the time accordingly, but that would lead to smaller and smaller adjustments every time as the round goes on. Come to think of it, that's already a problem; it's just obfuscated by the confusing timer setup. Adding/subtracting a fixed amount of time on every capture, or even a variable amount determined by how far ahead or behind the team is, is more in line with TF2 convention. You don't want to only add time, obviously, or rounds could potentially go on forever.
And finally: I think successfully capturing all five points should result in an automatic victory. But that's completely subjective and I can't think of any real justification for it other than it feels like it ought to be the case.