Ultimately the models are at the core of this hobby. Choosing the correct models is the part that will give you the most satisfaction. There are two aspects to this hobby, Modeling and playing games.

The models you choose will depend on your Ultimate interests. Are you interested in playing a particular game, or are you interested in collecting and painting interesting models? My personal favorite is Warmachine / Hoards by Privateer Press, both because of the sculpts that I enjoy painting as well as the ruleset.

For the War Gamer

If you are interested in playing the games then the most important aspects are the rules, theme and if you can find others to play near you. So here is a list of the most popular games and brief descriptions.

Warhammer 40,000

This futuristic sci-fi game is the 800-pound gorilla of the wargaming scene. Anywhere that you find a game store that sells tabletop miniatures, they will definitely sell Games Workshop models. This is a large scale army game. You will have dozens of models on the game table at a time sometimes hundreds depending on the game format that you are playing. If you want to command an army on a grand scale this is the type of game for you. Check the prices of Warhammer 40,000 starters on Amazon.

Pros:

You will be able to find a gaming group to join almost anywhere.
They offer easy customization with lots of options included right in the box
Highly detailed models (some of the finest detail around)

Cons:

Expensive (Games workshop is commonly considered the most expensive tabletop game publisher around)
Frequent updates to the rules can shift the balance of power between factions quickly

Warmachine / Hoards

This steampunk-themed game, by Privateer Press, is probably the second most popular tabletop miniature game around. It is also the game that I have played the longest. I really enjoy the mechanics of having a central piece, the warcaster, or warlock. This piece is what drives all of your other pieces and is simultaneously your strongest and weakest piece. It supplies all of the buffs to your force and if the other player takes it out you lose. This is what is called a skirmish game. It focuses on small groups of models that engage on an intimate scale and the game focuses more on achieving objectives than the total annihilation of your opponent’s force. Check prices for Warmachine on Amazon

Pros:

a smaller number of models used per game makes it easier to keep up with the hobby portion of assembling and painting your models
Very well detailed models are easy to pose in a variety of ways allowing you to truly make these your own
Simple play rules
Steam Punk (Need I say more)

Cons:

There is a large drop off from the number one position to number two position as far as finding a game (my local store doesn’t have a regular playgroup and I have to drive about half an hour to find a game)

Star Wars Legion

As you probably guessed by the name this is based on the Star Wars universe. It is a skirmish game that uses small squads to simulate battles. Check the prices of Star Wars Legion on Amazon.

Pros:

If you like Star Wars this is probably going to be the game for you
Simple straight forward rules

Cons:

The models are very simple and don’t have the same detail of some of the other games

For the Role Play Dungeon Master

Wiz Kids makes a line of Dungeons and Dragons miniatures that cover heroes and monsters alike. They are relatively inexpensive when compared with the tabletop wargaming miniatures. Check their current prices on Amazon

Reaper miniatures also have a line of miniatures for tabletop role-playing called the Bones line of miniatures. They aren’t quite as nice as the Wiz Kids models but they are also quite inexpensive. Check their current prices on Amazon.