It is surprising that I have yet to play Stronghold, the strategy genre is one of my favorites. Though I really don't know too much about Stronghold, other than the newer ones are a big hit and miss with the Stronghold fan base. So where do you guys recommend I start?

Stronghold is a fine game, and at its current sale price well worth picking up. It has free-form castle building and destruction, an exceptional map editor (with all the great fan-created material that comes with that), and has a nice balance of economic complexity with ease of management. If that sounds like something you'd like to play, then you should be happy with this game.

Between Stronghold and Stronghold Crusader, both have upsides and downsides. Stronghold original has a much superior campaign mode, and also has a really fun siege mode that was (for some unfathomable reason) removed in Crusader. On the other hand, Crusader has more units, more sandbox options, and introduces a castle vs castle mode with a half-decent AI to fight against. At regular price, the cost difference between Stronghold and Crusader makes me suggest Stronghold, but at the current sale price the difference between them is negligible.

What Darwin said & also, if you've ever played Age of Empires, it may look a little more complex with economics/taxes/food consumption but you can leave those alone if you want.

Every worker unit action is automated (after you've created a certain working building) & they respawn each time killed free-of-charge. Stronghold lives up to its name - defense being a major part of the game.

You can only play multiplayer co-op in Stronghold Crusader, not in Stronghold (only versus available), which is kind of odd :/

You mean u can only play co-op in Stronghold and only versus in Crusader?

Only the castle vs castle gameplay mode is multiplayer. All other gameplay modes are singleplayer only. Because there is no AI for castle-vs-castle in the original Stronghold, only versus gameplay is available. In Crusader, however, the existence of an AI means you can team up with a friend against them.

....right. So what kind of vs multiplayer has Stronghold 1? 2 castles on the same map one vs the other?

Essentially yes. Both players can build a castle, establish an economy, and raise an army. Last castle standing wins.

In Stronghold this mode is multiplayer only. In Stronghold Crusader, an AI was added and it can be played singleplayer, and it's one of the game's main gameplay modes.

Thank's for the input guy's! It sounds like a pretty interesting game then. I missed the sale unfortunately, but when I can I am definitely picking this up. Medieval is one of my favorite settings as well, so I am surprised I have passed this up over the years.

If that's the case then you'll probably enjoy the Stronghold games.