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1) Как сделать, чтобы когда игру уже установлена, при запуске инсталла выскакивало такое вот окошко? »

По-моему никто не ответил, а делается это

так

Код:

[Setup]
AppId={{B9B31282-6F8D-4D74-A8F2-24AE59608A9D}
AppName=My Program
AppVerName=My Program 1.5
AppPublisher=My Company, Inc.
AppPublisherURL=http://www.example.com/
AppSupportURL=http://www.example.com/
AppUpdatesURL=http://www.example.com/
DefaultDirName={pf}\My Program
DefaultGroupName=My Program
OutputBaseFilename=setup
Compression=lzma
SolidCompression=yes

[Languages]
Name: "russian"; MessagesFile: "compiler:Languages\Russian.isl"

[Tasks]
Name: "desktopicon"; Description: "{cm:CreateDesktopIcon}"; GroupDescription: "{cm:AdditionalIcons}"; Flags: unchecked

[Files]
Source: "C:\Program Files\Inno Setup 5\Examples\MyProg.exe"; DestDir: "{app}"; Flags: ignoreversion

[Icons]
Name: "{group}\My Program"; Filename: "{app}\MyProg.exe"
Name: "{group}\{cm:UninstallProgram,My Program}"; Filename: "{uninstallexe}"
Name: "{commondesktop}\My Program"; Filename: "{app}\MyProg.exe"; Tasks: desktopicon

[Run]
Filename: "{app}\MyProg.exe"; Description: "{cm:LaunchProgram,My Program}"; Flags: nowait postinstall skipifsilent

[Registry]
Root: HKLM; Subkey: Software\My Program; ValueType: string; ValueName: InstallPath; ValueData: {app}; Flags: uninsdeletekey

[_Code]
function InitializeSetup: Boolean;
var
  path: string;
  res: Integer;
begin
  Result:= True;
  if RegValueExists(HKLM, 'Software\My Program', 'InstallPath') then
    if RegQueryStringValue(HKLM, 'Software\My Program', 'InstallPath', path) then
      if FileExists(path + '\MyProg.exe') then
  if MsgBox('Запустить My Program?', mbConfirmation, MB_YESNO) = IDYES then
    begin
      Exec(path + '\MyProg.exe', '', '', SW_SHOW, ewWaitUntilTerminated, res);
      Result:= False;
    end
  else Result:= False;
end;