Any tips on leveling to 100?

Reverse pickpocket and pickpocket gold. Start out around 50 or so and work your way up to several hundred at a time. It XP gains are based on gold.

Thanks for the tips good sir... is there a particular spot that is good for pickpocketing?

Well, actually any NPC that is stationary is a good spot. Merchants, followers...

Save beforehand and often. This will get you where you want to be. Find one NPC, set up shop and get to work.

Pickpocket ring such as Silver Garnet ring will boost your skill.
Check all NPC pockets, sometimes there are some enchanment ring or amulet.
If you really want to fast leveling up pickpocket skill, training and pickpocket beggar in Windhelm.

Sven in Riverwood has a ring that improves pickpocketing of all things.
Make him your first target.
And like HanShield says above, Silda the Unseen in Windhelm is a pickpocket trainer. Train with her, then pickpocket your money back for about 8 easy free levels.

Thank you

I like to target small amounts of gold to start with at low levels.
Once you get good at that jewelry is the next step,it's a fairly high reward for a single piece.
Large amounts of gold or enchanted jewelry are hard targets,best to save them for later levels.

Also you can make very good fortify pickpocket potions,even with a low level alchemy skill.
The ingredients are somewhat hard to come by but once you get them you can get that enchanted jewelry,even at low levels.