Need some HELP!

OK, here's the deal.  I have 4 pups.  I keep any one of the four.  Jim gets any one of the remaining three (he wants a horseback trial type dog- bloodlines and performance of sire and dam indicate good potential for that in the males).  So, bottom line is, I have to decide which one for sure to keep.  Just to start.  I haven't marketed the dogs at all, but I have one for-sure buyer and one who's leaning hard to buy. So, one for me, one for Jim, one for Carter (male). That leaves the female (which I will keep in a heartbeat).  Here's where I need the help.  Choosing which one I want.  The boldest, most advanced and best looking tail is Hoss (not real name- identities are protected-lol).  Number 2 is Half Tail and he's physically identical- different coloration.  Number 3 is Pretty Boy- a tad smaller, much better looking, a shade less dominant than the other 2 males. Tails are all straight up!  Which one to keep. Is bolder better?  I have my own opinions- what are your thoughts?