[CLI] Improve documentation of `dart run --resident` and `dart compilation-server`

TEST=CI

Issue: https://github.com/dart-lang/sdk/issues/54245
Change-Id: I1806e1ef62e17d626e1bc37a10f67e6e8b402a0a
Reviewed-on: https://dart-review.googlesource.com/c/sdk/+/358741
Reviewed-by: Ben Konyi <bkonyi@google.com>
diff --git a/pkg/dartdev/lib/src/commands/compilation_server.dart b/pkg/dartdev/lib/src/commands/compilation_server.dart
index 931edaa..a01b683 100644
--- a/pkg/dartdev/lib/src/commands/compilation_server.dart
+++ b/pkg/dartdev/lib/src/commands/compilation_server.dart
@@ -16,15 +16,14 @@
 class CompilationServerCommand extends DartdevCommand {
   static const commandName = 'compilation-server';
 
-  static const commandDescription = 'Control the resident frontend compiler.';
+  static const commandDescription = 'Control resident frontend compilers.';
 
   static const residentServerInfoFileFlag = 'resident-server-info-file';
   static const residentServerInfoFileFlagDescription =
-      'Specify the file that the Dart CLI uses to communicate with the '
-      'resident frontend compiler. Passing this flag results in having one '
-      'unique resident frontend compiler per file. This is needed when '
-      'writing unit tests that utilize resident mode in order to maintain '
-      'isolation.';
+      'The path to an info file that the Dart CLI will use to communicate with '
+      'a resident frontend compiler. Each unique info file is associated with '
+      'a unique resident frontend compiler. If this flag is ommitted, the '
+      'default info file will be used.';
 
   CompilationServerCommand({bool verbose = false})
       : super(
@@ -41,7 +40,7 @@
 class CompilationServerStartCommand extends DartdevCommand {
   static const commandName = 'start';
 
-  static const commandDescription = 'Starts the resident frontend compiler.';
+  static const commandDescription = 'Start a resident frontend compiler.';
 
   CompilationServerStartCommand({bool verbose = false})
       : super(
@@ -82,9 +81,7 @@
   static const commandName = 'shutdown';
 
   static const commandDescription = '''
-Shut down the resident frontend compiler.
-
-Frontend compilers stay resident in memory when using 'dart run --resident'. This command will shutdown any remaining frontend compiler processes.
+Shut down a resident frontend compiler.
 
 Note that this command name and usage could change as we evolve the resident frontend compiler behavior.''';
 
diff --git a/pkg/dartdev/lib/src/commands/run.dart b/pkg/dartdev/lib/src/commands/run.dart
index 4e748c9..1906e75 100644
--- a/pkg/dartdev/lib/src/commands/run.dart
+++ b/pkg/dartdev/lib/src/commands/run.dart
@@ -52,12 +52,17 @@
         ) {
     argParser
       ..addFlag(
-        'resident',
+        residentOption,
         abbr: 'r',
         negatable: false,
-        help:
-            'Enable faster startup times with the resident frontend compiler.\n'
-            "See 'dart ${CompilationServerCommand.commandName} -h' for more information.",
+        help: 'Enable faster startup times by using a resident frontend '
+            'compiler for compilation.\n'
+            'If --resident-server-info-file is provided in conjunction with '
+            'this flag, the specified info file will be used, otherwise the '
+            'default info file will be used. If there is not already a '
+            'compiler associated with the selected info file, one will be '
+            "started. Refer to 'dart ${CompilationServerCommand.commandName} "
+            "start -h' for more information about info files.",
         hide: !verbose,
       )
       ..addOption(