Regarding your question about what tools should be in the toolbox, the parts list includes the following items:
Monkey wrench
Spark plug wrench
Screw driver
Oil can (accessory)
Tire repair outfit (accessory)
Pump clips, per pair
Tire pump
Chain repair tool (accessory)
Open end wrench 41/64, 3/8, 5/16
Open end wrench 45/64, 29/64
Open end wrench 49/64, 37/64
Double end socket wrench (accessory)
Double end socket wrench pin (accessory)
Pliers
Automatic oiler pump test plug (accessory)
Tool roll
Automatic oiler cam adjusting screw wrench
Valve sleeve and head adjusting cone wrench
Valve tappet screw wrench
Cylinder stud nut wrench (accessory)
Cylinder head stud nut wrench
Cylinder stud nut wrench handle
Alemite grease gun
Alemite grease gun hose
Of course, having a list in the parts book doesn't mean that all of the above would have been supplied with the motorcycle. I've never seen even a photo of an original 101 Scout tool roll with tools; if you find one, please share it with us!
dkgoz