It's fairly easy to imagine a significant palisade as described in the reading on the south and westward facing portion of the old fairgrounds. We know Poindexter was slowed, but Colonel Brown seems to have gotten himself into place rather quickly. I have no way of accounting for this unless they arrived with an open gate or the south end of the grounds was a sturdy, yet not impregnable defense.......
Palisade or fence? The West and South side of the Union complex I'm guessing would have been part of the pre-war fairgrounds that faced Boonville, so perhaps it had a rather stout fence. Did the Union reinforce this fence? Yet there were gates along this fence where the roads to Boonville met the complex.
Acting as a Monday morning general, I'm thinking that the difference was in the leadership of the opposing forces. The union forces were Union home guards, with how much training (?), but probably more than the MSG. And they were fighting behind cover which with the rain had to have been a muddy mess, and they were local, so there is the "fighting for home" factor. And they had military weapons. The MSG outnumbered the home guard by what ratio? 5/1?, 7/1? but probably were fairly new recruits with little to no training and once the bullets started to whistle around their ears, were content to hug a tree rather than close with the enemy. They were largely armed with squirrel rifles and shotguns and attacking a fortified position where they couldn't see their enemy. I'm thinking with these factors, the odds were pretty even.
So it falls to the commanders:
Eppstein, from his actions at the fort and later in the war seemed to have proven himself a capable and decisive commander. Brown was perhaps more excitable, a firebrand, emotional, (witness his actions at the first Battle of Boonville), not as patient or capable as to what was needed in operation with raw troops attacking from different directions. He didn't lack courage though, and lead from the front, but he needed someone behind him urging his men forward to overwhelm the fort. A well trained man can get off 3 rounds a minute with a musket. How fast can a man run a 100 yards? If Col. Brown could have massed his men in the orchard, he may have been able to get them up to the base of the fort before the home guards a second shot off.
And Poindexter failed him in failing to appear in time, and we don't know why he was late. So, perhaps the better battle plan would have been for Brown to have waited to until Poindexter started the battle, pin the home guard down to the West side of the fort, then he and his brother begin their joint attack at the East end. Or, have his brother, someone he could trust, take half/some his men and join with Poindexter as the second in command and attack the fort with him. So then Poindexter/Capt. Brown attack from the Boonville side, and Col. Brown attacks from the Lilly orchard. I think the MSG could have taken the fort, if it was a combined and coordinated attack from both ends. At this point in the war, the MSG didn't have the training to do this.
BTW, We have to assume that Brown and Poindexter rode to Boonville, We know Browns men left their horses at the Stevens home. Where did Poindexter "park" his horses?