I too think the handlers do a good job of letting everyone know that the character will have to leave at a certain time (so if you do decide to stand in line, you know there's no guarantee). But a thought just occurred to me - if a family or two is as inconsiderate as the OP mentioned (I consider it inconsiderate - others disagree), how is the handler supposed to determine where the line should end?
In other words, if there are only 2 families ahead of you and you are the third person/family in line, the handler says "5 more minutes", you might think that you have a shot. But if the first family takes up all 5 minutes... well, then you are out of luck.
That's why I think it is inconsiderate of families or individuals to take up more than what I would think is a reasonable amount of time with a character... of course, who's to determine what is a reasonable amount of time? Two pictures? One picture and an autograph? One picture per child or adult in the group? It's too difficult to determine.
I usually don't even bother when there is more than 4 people in line, unless I see the character just arrive (so you know they will be there for at least 5 minutes). I've only waited for a character meet 4 times - twice with Pluto (both times, just one person getting their picture taken, no line), once w/ Minnie (as I described in my prev post) and once w/ Sorcerer Mickey. I consider the one w/ Sorcerer Mickey the best experience. I was at DCA and they have the Drawn to the Magic stage in the Hollywood Backlot area. We were walking and I saw Cinderella with a line of people, then we saw Woody and then Mickey. I figured out that the 3 characters are part of the show. Either I could stand in line with maybe 8 people in front of me, or just wait until the next show. I chose the latter and went to use the restroom while my sis stayed in the DTTM area. When I got back, the characters (and lines) were gone - I asked my sis if everyone in line got to meet Sorcerer Mickey and she said no.
I sat in the seats on the right because I knew that Mickey would be on the right - so as soon as the show was done, and the handler mentioned something about meeting with the characters, I hopped into line and was the 4th person.
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