I finally have enough figures to field an army of hobbits and I am playing around with two options:

First of all the basics:
Frodo of the Nine Fingers to serve as a banner with elven cloak.
Meriadoc, Knight of the Mark on Pony and with the Horn of the Riddermark
Paladin Took
Lobelia Sackville-Baggins
12 Hobbit Militia
4 Shirriffs
8 Hobbit Archers with one Signal Horn

I am trying to decide between the following two options
Gandalf the Grey
Samwise the Brave with elven cloak
--or--
Strider
Farmer Maggot

Any opinions?

I'll probably be wiped out either way, but it will be fun.

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You really need more numbers. For Hobbits it's absolutely essential that you have as many models as possible.

As for Aragorn vs. Gandalf, I'd take the Grey Wizard, simply because his Blinding Light will be extremely useful.

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"There are few left in Middle Earth like Aragorn, son of Arathorn." - Gandalf, Many Meetings

You need gandalf, and 50 units. Also, a few dunedain don't hurt.
Gandalf
Lobelia
5 dunedain w/ spear

29 shirriff
13 archers
1 archer w/signal horn

50 units, 497 points, 8 might

The only thing I was thinking about Gandalf vs Aragorn is Aragorn's constant supply of Might. I can use his might for heroic moving and shooting. Heroic moving, because the hobbits are so slow that when I need to move first, I NEED TO MOVE. Heroic shooting because of the throw stone ability. Get the hobbits close enough and turn all the hobbits into shooters. That assumes Aragorn has a bow.

I am also using an Excel sheet I downloaded for the army building. Are heros counted when figuring the 33% archer rule? The excel I am using does not seem to do so.

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Heros don't count towards bow limit.

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"I am the Flying Spagetti Monster. Thou shall have no other monsters before me"
-FSM.

theavenger001 pretty much nailed it