First, I like the idea of creating a scenario like this and the map is pretty good. Your story of elementary conquests made me reminisce on my school days empires. I hope you don't consider it a copyrighted idea because now I'm thinking about doing something along the same lines lol. On the other hand, I feeled compelled to tell my story because I see you think y'all were the best. Sorry man, but I think not

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I'll make this as BRIEF as possible, otherwise it'll be a novel so here it goes.
Venable Village, Ft. Hood Texas: mid 1986-88
Moved there when I finished kindergarden, learned to ride a bike (calvary), explored all the Venable, Pershing Park and South Nolan Creek from S. Ft. Hood st. west until I hit hwy. 190, northern tip of Willow Springs, Patton Park, 440 plaza areas(I'll post a map). Made a few friends, even more enemies, and learned about the Venable-Pershing rivalry.
88-90:
Alliance between MacMichaels cir. (my street), South end of Efird st. where most my friends lived, bullies and rival occupy the center and North end, and a good portion of Wainscott Ave., the largest st. in Venable. Lopez Loop is conquered and all enemies subjugated or forced to pay tribute, usually as weapons making material, bicycle parts, and kid's currency (candy, kool-aid packs, and toys, G.I. Joe's in particular

) The barbarians (bullies) on Efird are virtually destroyed, large amounts of booty taken and put in a abandoned trucker trailer on Venable dr. It would become our storehouse until it was taken a year later before we could get all our stuff out

.Barbarians on Wainscott and Efird try to revolt, crush again and brutally punished (beat them with thorned sticks and stole their bikes). Hawsey cir. taken with little effort. Churchhill st. put up a good fight but I invented bicycle blitzkrieg to finish them. My brother Christopher learns to ride a bike, just in time too. Pershing Park finally realizes what's been going on and sends a large force (about 20) and begins patrol around the creek, the border between Venable and Pershing. I counter with garrisons at the Bat Cave (a thick mass of vines and bushes hollowed out at the the creek SE of MacMichaels cir.), the Rock Pile (large pile of gravel lefted by construction on the westside close to the creek, protected by rough terrain and an ideal spot to launch a surprise attack against Pershing's left), and lookouts at the Deep Hole (a big inlet, by comparison to the rest of the creek, where a drainage ran to it from Pershing. It's directly S. of MacMichaels cir. ). By late 89 Venable is in my total control and poised to invade Pershing after the winter.
90-91:
Pershing Park, having been idle during the winter was attacked in early spring, before they anticipated any action. A barrage of artillery (rocks or water balloons) preceded an infantry attack from the Rock Pile and calvary down the main sidewalk from Efird to Pershing. An attack from this direction was not expected because of the terrain advantage the Pershing's enjoyed. Their village is twice the size of ours and the same ratio of manpower. The sidewalk from the S. on our side is flat ground but on their's, all up hill. So once the bikes crossed the bridge of the creek and got to the top of the first hill, we broke left an rode the crest of the small lower hill. This concealed our movements thanks to the bigger hills above us until we got to the big playground on the westside of Pershing. From there, we rode up the sidewalk into Pershing completely surprising them. Letting loose a hail of balloons, rocks for more stubborn foes, and steel reinforment rods thrown into spokes for anyone trying to escape. In about 30 minutes, their right flank had been obliterated and no one was able to send word for reinforcements. At the same time as the bike attack, the infantry made it after a long walk to east Pershing, using the drainage ditches and hilly ground to hide themselves. They were told to split in two when reaching the Pershing left, one force hitting from the east, another crossing the pedestrian bridge in western Pershing into their heartland. They were successful, but a few managed to notify the bulk of their army(around 45-55). The plan was for the infantry to complete the initial surprise attacks, penetrate to Hoover Hill rd. without stopping for spoils and meet the bikes at the corner of Cutler and Hoover Hill. The bikes meanwhile were to swing around to the big playground and destroy their "early warning system" and blitz between the north and east wings of Pershing. This was achieved but I saw their main force gathering and beginning their way UP Hoover Hill toward the infantry. Hoover Hill is pretty steep, going down on a bike u can easily keep pace with cars. I sent my friend Billy to inform the infantry of the coming threat and fallback to Rowe st. and hold there. My cav went down to the main drainage ditch west to the ped. bridge and climbed the hill at the end of Kildea st. then engaged the enemy with the infantry. They didn't organize there forces well so when I met them they were extremely outnumbered. We were low on ammo by this point so I told the infantry to retreat to home by way of the main sidewalk, collecting all the spoils along the way. I then charged downhill at the Pershings, spending the remainder of the ammo and taking out as many as I could. 2/3 the way down I turned into the shopette to access damage and waited for their cav charge. Hiding behind the shopette the enemy charge did not see us so I charged again, this time to their backs. Catching them at the bottom of the hill, we drew our thorn swords and started to inflict some serious damage, most retreated, some leaving their bikes and all. We collected the spoils and headed home. The Pershing's were forever broken and the The Pirate Empire was born. I started to consolidate, suppressing rebellion's here and there but before I could finish, I moved again to Germany.