topley wrote: To a newbie like me seems a little odd that breeding to sell and breeding to run would be mutually exclusive. Shouldn't the ones that sell be the ones with the best chance to run? Although I am starting to understand the intrincacies that make the difference...
The yearling sales market wants three things consistently and various other things from time to time. It consistently wants (a) large yearlings with (b) good conformation and (c) an "acceptable" pedigree. Presently an acceptable pedigree may mean either that the runner will mature early with a good chance of winning/stakes at 2, or that the runner is from a young sire who may be the next Storm Cat and the buyers want to have a crack at the next big thing. Generally the pedigrees of the first category are already known (Storm Cats, Mr Ps, etc), the proven sires that have repeated juvenile success tend to be very pricey. The second category are all based on chasing a dream.
With respect to Pleasantly Perfect--on paper that is a nice cross, not as nice as Pleasant Tap for reasons I'll outline below, but your goal in this is to make a profit. Your mare is from a stakes-producing family, but not a strong enough stakes producing family to get a lot of attention in Kentucky on a $40,000 fee. You might cover the stud fee, or the foal might RNA. In Maryland, the foal will almost certainly not make a profit for you (in the $55-60k range). Based on that alone, he's a pass. Although a nice pass.

Question for you, I noticed in the examples you gave that Pleasant Colony was on the female side on the majority of them. Would it make a difference to reverse it or is it the cross that matters?
Yes, it does make a difference. In another thread, Pete and KAL discuss and debate whether Seattle Slew plus Mr P is a better match than Slew's son AP Indy and Mr P. It's worth a read. Having a pair of sons of the big-name stallions, rather than the stallions themselves, doesn't always work but in this case I think it will and here is why.
With respect to Pleasant Colony, Dixieland Band, Pleasant Tap, and Citidancer there are a couple of things going on. PC over DB was tried only 3 times, while DB over PC was tried 20 times with 19 individual mares. In this case, I think it was a numbers game. So far as Pleasant Tap and Citidander: Usually, looking for an inherited affinity or "nick" between a stallion and a son doesn't work as expected, and a reverse affinity between a sireline and another sireline (e.g. PC over DB vs. DB over PC) REALLY doesn't work as expected. While a breeder might try it, there is no guarantee for success just because it worked the other way around. But Pleasant Tap, against all odds, proved himself to be VERY useful with Dixieland Band mares.
Of all the well-known Pleasant Colony sons at stud today, only Pleasant Tap is free of Northern Dancer. Pleasantly Perfect, Forbidden Apple, Behrens, and Colonial Colony ALL have a son strain of Northern Dancer within five generations. Pleasant Tap lacks that key strain, and when mares with a son strain of Northern Dancer are sent to him, the resulting foals perform WAY better than average. A quick peek at the broodmare sires of his top runners yields Northern Dancer, Nijinsky, Soverign Dancer, Dayjur, Polish Navy, Nureyev, and Dixieland Band. At least half of the strong runners whose first broodmare sires are not ND-line have a 2nd or even 3rd broodmare sire who is ND-line. It is reasonable to assume that Citidancer, as a direct tail-male to ND, would work with Pleasant Tap. This cross does not appear to have been tried.
But wait, there's more! Remember Nureyette, the Nureyev over Tentam mare? She is bred on an extremely close cross to Citidancer. Nureyev is Northern Dancer over a Forli (Hyperion-line) mare, while Dixieland Band is Northern Dancer over Traffic Judge (Hyperion via Alibhai). Citidancer and Nureyette are not quite but VERY close to what I would define as genetic siblings, with two grandparents being the same. Given that bit of knowledge, and that one of Pleasant Tap's best runners is out of a mare that is nearly a sibling to Citidancer, it is even more reason to suspect that Pleasant Tap over Citidancer will be successful.
Whew! That was a rather long-winded response, but I hope it answered your question on sires and inherited "nicks."
Thanks again. Any opinions on the stallions I offered as suggestions?
I'll try to answer this one later.