What land should I join?

My character Andrew Greyscar is a swashbuckler. He has worked as both a mercenary and contract killer. There are few things he values above money, and he has dealt in shady businesses before.
What land would fit Andrew well? In between games Andrew is working for pay in the drega mire swamps. I have only attended 2 events so far.

Also what advantages are there to joining a particular land? Should my character even join a land?

Joining a land is really up to you. The lands themselves have a distinct role play aspect to them between events, but ultimately at the game it boils down to who you feel most comfortable around. I'd suggest meeting with as many vassal and mobility from each land, and talk to them. Get a feel for what fits you better as a player more than a character. I'd suggest posting on the Dragons claw forum to try to reach out to members of the lands to meet with people. If you are struggling, any one of the New Player Marshals can help introduce you.

There's a prominent letter on the Dragon Claw board describing all of the lands for newcomers should you like to see it. www.knightrealms.com/forum/The-Dragons-C...ers-to-travance.html

Also look into the Baronial Library! It's all common knowledge stuff IG that you can know as your PC.
www.knightrealms.com/in-game/the-baronia...ony-of-travance.html
www.knightrealms.com/in-game/nobility.html
www.knightrealms.com/in-game/the-baronia...world-of-arawyn.html

There is no requirement for joining a land. There is plenty of things to do and not a thing requires being part of a land. Given you have been here for two events, I STRONGLY suggest not even thinking about it right now. There is far more stuff going on that being independent makes sense... and actually experiencing the game world a bit more.

Each land has its own personality- complete with strengths, weaknesses and quirks... of its residents. All have reputations that are rightly deserved or a big misunderstanding (depending on who you talk to) in where they sit politically in game or in how accepting of new folks running around their areas.

Learn them. Experience them.... Find out for yourself about each one and make your own judgement/decisions on who is alright in your book as your PC and who can go fly a kite in a thunderstorm or something equally dangerous. Bottom line, let experience and knowledge help you decide.

As Matt mentioned, it boils down what you are comfortable with and what just makes sense.

Openly calling yourself a Mercenary already paints you in a certain light as some lands have In Character Issues with such folk and others openly welcome them. Part of the fun is figuring out who is who... and where you are likely to get along alright once folks know you are a Merc (and sometime Contract Killer).

Engage the other Mercs in game- and there are more than a few of us (Storm Runners of Ostcliff and the semi-independent Blood Spirits are two of the more (in)famous ones) so ask around. Someone is bound to give you some info. No telling how good it is but that's part of the fun and the beauty of Role Play.

Take your time. it took me three years to decide.