I don't do them often, just for the BC with some friends for a pick-4. It's all give and take.
For example, this year my mom (yes she is included) argued with me all the day before about having Miesque's Approval on the ticket. We all told her she was acting like a fool and we left him off. For the Turf, I was the only one of our group of four who wanted Red Rocks, and we left him on because I wouldn't budge.
Sometimes it works out, sometimes it doesn't. Obviously, you won't see every race eye to eye, but there is some give and take involved in pooling money. I think it takes the very right kind of personalities matched to make these work.
If you stick with his single and it loses and you hit 3/4, you'll be mad. If you push him to add another horse, and drop 2 other horses he likes in another leg and you hit 3/4 missing the now shorter race, he's mad.
I only do them with really good friends of mine who all want to get in together to maximize our chances but won't stop talking to each other if it heads south after the first race (ie, i got one "i told you so" after the mile, and that was that.)
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