I too have the dilemma of how much to feed and how to keep them happy while feeding them less to keep their weight down.

This is what I'm doing and seems to be working: I got a measuring cup from the vet (basically a regular cup with lines on it) and read the back of the weight management food. I figured that with all the cats, they'd need a little over 5 cups a day (Allen & Harry need more, Abby & Flutter lots less) I simply cannot get them to agree to their own bowls, so That 5 cups a day goes out and whoever is quick enough to eat it first gets it. But thats not been a problem because all 5 kitties are at the feeding table at the same time, so its not as if Abby and Flutter can pig out on Allen's food while he's not there.

Anyhooo..... Hubby puts out 3 cups in the morning. I come along two hours and divvy out another 1/2 cup (which amounts to just a snack for them) Then I divvy out another 1/2 cup in the afternoon when I'm home at lunch. Then at dinner time they get one cup while we hoomans attempt to eat in peace. Lastly, they all get a can of wet food thats spread out between all 5 kitties (and Nicki gets some of that too ).

So, in short the feeding schedule is now as follows:
5:30 AM = 3 cups
7:30 AM = 1/2 cup
12:00 PM = 1/2 cup
5:00 PM = 1 cup
8:00 PM = 1 can divided as a treat among all kitties

This routine is working very well because they still get food throughout the day and don't feel like I'm starving them (though Harry's got a strong opinion on that one ) I already see a difference in all of their weights, and its only been a month or so that we've been doing this.