Proof of concept, now to figure out how it works!

SentinelPlugin/build.gradle

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+plugins {
+    id 'java'
+}
+
+group = 'me.trouper.sentinel'
+version = '1.0-SNAPSHOT'
+
+repositories {
+    mavenCentral()
+    maven {
+        name = "papermc-repo"
+        url = "https://repo.papermc.io/repository/maven-public/"
+    }
+    maven {
+        name = "sonatype"
+        url = "https://oss.sonatype.org/content/groups/public/"
+    }
+}
+
+dependencies {
+    compileOnly("io.papermc.paper:paper-api:1.21.4-R0.1-SNAPSHOT")
+}
+
+def targetJavaVersion = 21
+java {
+    def javaVersion = JavaVersion.toVersion(targetJavaVersion)
+    sourceCompatibility = javaVersion
+    targetCompatibility = javaVersion
+    if (JavaVersion.current() < javaVersion) {
+        toolchain.languageVersion = JavaLanguageVersion.of(targetJavaVersion)
+    }
+}
+
+tasks.withType(JavaCompile).configureEach {
+    options.encoding = 'UTF-8'
+
+    if (targetJavaVersion >= 10 || JavaVersion.current().isJava10Compatible()) {
+        options.release.set(targetJavaVersion)
+    }
+}
+
+processResources {
+    def props = [version: version]
+    inputs.properties props
+    filteringCharset 'UTF-8'
+    filesMatching('paper-plugin.yml') {
+        expand props
+    }
+}

SentinelPlugin/gradle/wrapper/gradle-wrapper.properties

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+distributionUrl=https\://services.gradle.org/distributions/gradle-8.8-bin.zip

SentinelPlugin/settings.gradle

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+rootProject.name = 'SentinelPlugin'

SentinelPlugin/src/main/java/me/trouper/sentinel/plugin/SentinelPlugin.java

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+package me.trouper.sentinel.plugin;
+
+import org.bukkit.Bukkit;
+import org.bukkit.command.Command;
+import org.bukkit.command.CommandMap;
+import org.bukkit.command.CommandSender;
+import org.bukkit.command.PluginCommand;
+import org.bukkit.command.defaults.BukkitCommand;
+import org.bukkit.plugin.java.JavaPlugin;
+
+public final class SentinelPlugin extends JavaPlugin {
+
+    public static void initialize(JavaPlugin loaderPlugin) {
+        loaderPlugin.getLogger().info("Hello from dynamically loaded Plugin!");
+        Bukkit.getScheduler().runTask(loaderPlugin, () -> {
+            PluginCommand command = Bukkit.getPluginCommand("demo");
+            if (command != null) {
+                command.setExecutor((sender, cmd, label, args) -> {
+                    sender.sendMessage("Hello from dynamically loaded plugin!");
+                    return true;
+                });
+            }
+        });
+    }
+}