Level 1
ST 5 PE 5 EN 9 CH 1 IN 9 AG 6 LK 5
Speech, Barter, and Small Guns
Bobblehead (Medicine)
Level 2
Sneak +3 (20), Small Guns +3 (35), Lockpick +5 (20), Speech +3 (25), Explosives +5 (20)
Lady Killer/Black Widow
Bobblehead (Intelligence)
Level 3
Lockpick +5 (25), Speech +5 (30), Repair +5 (30), Science +5 (30)
Little Leaguer
Level 4
Small Guns +5 (40), Energy Weapons +5 (20), Unarmed +2 (25), Barter +3 (25), Science +5 (35)
Comprehension
Level 5
Sneak +5 (25), Lockpick +5 (30), Repair +5 (35), Science +5 (40)
Entomologist
Ant Sight
Level 6
Energy Weapons +4 (26), Lockpick +3 (35), Repair +5 (40), Explosives +3 (30), Medicine +5 (40)
Bloody Mess
Level 7
Sneak +6 (31), Energy Weapons +4 (30), Medicine +10 (50)
Toughness
Level 8
Sneak +9 (40), Lockpick +5 (40), Explosives +6 (36)
Commando
Level 9
Unarmed +8 (33), Explosives +4 (40), Barter +3 (28), Melee Weapons +5 (25)
Strong Back
Bobblehead (Endurance)
Bobblehead (Luck)
Level 10
Unarmed +5 (40), Barter +6 (34), Melee Weapons +9 (34)
Finesse
Level 11
Small Guns +6 (46), Barter +8 (42), Melee Weapons +6 (40)
Size Matters
All skills need to go up to 40 except for: barter at 42 (one less skill book for this skill than normal), big guns at 25 (size matters brings it up to 40), energy weapons at 30 (cyborg brings it up to 40), and speech to 30 (yew's bear charm brings it up to 40). Collect all skill bobbleheads to bring them all up to 50, then collect the appropriate skill books, or even use skill points if you would desire.
Since you would only be at level 11 (ie. 19 levels to go until level cap) it isn't necessary to get every single skill book, and more importantly, have INT at 9+1 AND educated AND comprehension. It is easier and more efficient to just have comprehension. And again, since there are 19 levels until the level cap, it's probably a waste to have INT at 9+1 in the first place.