There are only 2 ways that Kendall gets on for the top of the order as you say is important. Either the pitcher gets out and then Kendall leads off the next inning (wouldn't you rather have your leadoff guy leadoff?)
Kendall still gets out 65% of the time or so. I'd much rather have the pitcher make the 3rd out than Kendall make the third out and have the pitcher leading off.
OR the pitcher gets out with less than 2 outs and Kendall gets on to extend the inning...in that case, wouldn't you rather Kendall get that hit hitting 8th and then the pitcher bunt him over?
No I'd rather have the pitcher bunting guys over for Kendall to drive them in because Kendall is a low power high OBP extreme groundball hitter. It is much better for him to come up with 2 outs and a runner on 2nd than 1 out and a runner on 1st and the pitcher behind him.
It is never better to have the out first and then the hit as opposed to the hit and then the out. So what exactly are you talking about? You don't want guys on for your leadoff hitter, you want them leading off.
Not when your leadoff hitter has 20+ HR power in his bat.
There are exactly two situations where this setup fails.
1) A runner is on 2nd or 3rd with 2 outs for the pitcher. In this case I'd much rather have had Kendall up.
2) The 8 spot leads off the inning. In this case I'd rather Kendall gets his single or out before the pitcher so he can bunt.
Every other situation in the game I'd rather have Kendall 9th and the pitcher 8th. The every other situation has happened a whole lot more than those two situations.