Since it's non-negotiable, first do your research, as suggested. Beyond the laws/logistics of the country, it's key to understand the school's housing practices. If you'll be arranging your own housing, it's not much of an issue. But if the housing is provided directly by the school, you should ask early on about the rules re pets. In some schools, pets are absolutely not allowed in the school housing. Find out before you get too far into the process - don't waste your own time (or the recruiter's).

I agree with most of what's been said, except for the advice that you not mention your girlfriend in the recruiting process. True, the school won't extend benefits if you're not married, but if they understand your situation they will be in a better position to set you up. Such as by putting you in the housing area that has more committed couples, instead of the apartment block that's all partying singles. Such as by passing her name on to friends who might be able to employ her. Such as by giving you advice about how to navigate legal situations and social norms. Even as simple as telling you, 'hey, that's no big deal here', or 'whoah, living together in xyz country is really hard'.
Not to mention the very obvious tiny detail that when they pick you up at the airport, they'll be prepared for 1 person. Having a girlfriend in tow will make you look like you've been hiding something, which suggests dishonesty. Not a great start.

There won't be too many more schools registering. Generally schools have already decided which fairs they'll attend.
And even if there are 150 schools there, there will be a good fair few of them which you won't be interested in or which won't have an opening for you.
And if you're thinking of dropping your CV into every recruiter's mail folder, think again. Unless you attach a personal note, that unrequested CV is not likely to get much air play. Remember that the recruiters will already have access to all your documents through the Search database - a recruiter who's doing their job right will already have been through them all and prioritized who they want to contact. If you're not already on their list, dropping a duplicate CV into their folder isn't likely to change anything. Better to target the schools you really think have potential for you, and write them a nice personal note / cover letter explaining why you and the school are such a great match.

How long is a piece of string?
The most active recruiting period is probably December through February, but it all varies by school, by position, by applicant. My school is already actively engaging with a few choice candidates, but we are also pretty much not engaging at all with candidates who offer less of what we're looking for. Those same candidates might get more attention later on, if we can't find people who tick all of our boxes. Or they might fall out of consideration entirely when we hire someone.

The real question is when will things heat up for you personally? It's hard to say. For absolute top-notch candidates, maybe only 10% of the field, we're already in active recruiting season. For the bulk of candidates, things will heat up later, more like Dec/Jan. And for the 'in with a chance' crowd, they may have to wait until the main rush passes, as in when schools have hired most positions already and the very best candidates are already taken.

But any of that can change for unknowable reasons. Occasionally the most incredible superstar teaching couple gets overlooked... and why? Occasionally the inexperienced newbie snaps something up early on. Far too often, low quality schools actively recruit naive newcomers, who only realize what's happened after it's too late.

Good luck. There's something out there for just about everyone.

Legal repercussions vary and would generally be minimal if there are any. The school is probably not in any sort of position to enforce an expectation that you pay them back their expenses, nor anything like that.

Cheery's right, the real repercussions are in pissing off groups and individuals you may need later. I've personally seen teachers take mega-hits years after doing this sort of thing, losing out on jobs they would otherwise have gotten, just because someone knew what they had done and wasn't afraid to share it. Schools don't like getting burned, and they will freely tell other schools to avoid you on the grounds that if you did it once, you'll do it again.

Not to mention the very real possibility that if you duck out of a contract with School A in favor of School B, School A might then tell School B about it, and School B could cancel your contract on the grounds that you recruited and signed under false pretenses. It's a standard rule in recruiting that once you sign, you have to stop looking - if you're seen to still be looking, or even worse if you sign another contract, you can be sacked from your job before you even get there.

And yes, international schools are very closely connected. We all move around pretty frequently, so there's always someone at School A who is friends with someone at School B, so this sort of thing easily gets around the grapevine.

Best advice: look carefully, consider carefully, accept an offer that pleases you, and don't look back.

None, really. Few offer summer schools, and those that do tend to staff them with existing teachers.

It can be quite hard to get positions in popular cities like Paris, London, etc. Tons of people are extremely keen to live there, so competition is fierce and packages tend to be on the low side. You'll be in the queue with colleagues with 30 years experience and Masters degrees and pensions from home to supplement their meager European income.
The story is quite different in other European cities. Try countries in Western Europe. Former USSR satellites. Places really far north. Competition is much lower, packages often significantly better, and quality of life very similar. With your credentials, you'd probably find a decent position.

Wouldn't worry about it too much. Especially if it's just the name, and the rest of the letter includes correct details about the school, its environment and why your skills match their mission.
Definitely don't call attention to it, but if the time comes to submit a second application, fix it.

Sadly, it seems that schools in general are notorious about not getting back to applicants. If you send the application to the right address, you have to take it on faith that it was screened. If the school is interested, sooner or later you'll hear something. If they're not, you might never hear. And the time frame can be quite long - if you're someone of interest, but not at the top of the school's list, they might consider and interview several other candidates before deciding whether to contact you. Or sometimes, even if you're at the top of the list, the school's process doesn't start until long after you've submitted an ap.

In my view, it's rather wrong not to send any reply at all. On the other hand, I sympathize with the time frame issues. Recruiting is a fluid process and while it's excruciating to be sat waiting on the other end, there are real reasons why schools can take what seems forever to make a move.

Apply to my school and you'll get a sort of automated response, thanking you for your interest and indicating that we'll contact you if we're interested. In other words, don't expect any more contact if we're not interested. There's no time frame given, as generally we don't have one; we hire as we find the people we want, whether that takes days, weeks or months. And while you might not be our first choice, we do take notes on all applications, so we know who's next in line if our first choices don't work out or a new position opens up.

Protocol on your end? Wait at least a week if you don't get any response at all, then contact the school and gently inquire. No response after that? Give up, unless that school is everything you've ever dreamed of.
If you do get a response to your initial application, but it's vague (like my school's automatic response), wait at least 2 weeks and then gently inquire.

And never give up hope. Situations change, positions open and close and open... You might hear nothing for months and then BOOM, there it is, a request to interview.

Which all adds up to why I recommend fairs for most applicants. You're there, the school is there, good things can happen quickly. For experienced and excellent educators, it can be easy to get hired through e-mail applications and Skype interviews. But for those newer to the circuit or with smaller halos around their heads, fairs can be the easier route.

I don't know enough about Bangkok to know where the different schools recruit, but I do know there is quite a number and range of schools in the city. There will surely be some willing to look at younger candidates. But don't limit yourself to Bangkok. Spread out those applications, cast a wide net.

The Iowa fair tends to have higher numbers of younger applicants. I would expect schools there to therefore be more open to candidates with less experience. There are also fairs in June/July where schools are looking to fill final openings. The data is clear - experienced and married couples get jobs at the highest rates in the Jan/Feb fairs, while younger and single people have better rates in the June market. But that doesn't mean you can't get hired earlier. Lots of people do. Don't mistake a trend for a certainty, just use that data to pick a fair. And then, yes, apply to every opening that suits you. Apply early, and apply again once time has elapsed and the opening is still there. Recruiters have been known to give closer looks to candidates who are showing persistent (not pushy/demanding) interest. After all, if you really seem to want to come to my school, that's a point in your favor over someone who just sent a single email and gave up.

I wouldn't mention that you're seeking a Masters unless you have already taken several of the courses, and maybe not even then. It's just not relevant at the point of hiring. If you have one, that's relevant. If you're moments away from finishing, that's relevant. If you have a sincere ambition to get one, you're in a large group, most of whom will never finish the journey. Also, you may put doubts in a recruiter's mind that you're spreading yourself too thin. New to teaching? Means extra hours prepping. All those extra hours on after school activities? Young and potentially out there in the social scene? More hours gone. Add in a Masters program? Where will it all fit? Can this guy be counted on to keep all the balls in the air without dropping any?

As for applying by mail only, I'd missed that part. You're right, you have a high chance of seeing your CV languish in the 'too difficult' pile. Your weakness (inexperience) can only be countered by a recruiter meeting you in person, or even via skype, and vetting you carefully. As a recruiter, I wouldn't want to take a chance on someone with so little experience unless I could reassure myself that this person really was a rising star. I'm not sure what exactly to do to get your CV to stand out. Again, focus on the less desirable schools and locations. Contact schools repeatedly without being pushy/demanding. Wait until later in the hiring season when the top-notch candidates have been snapped up and schools are looking to fill their last remaining spots. But really, my advice would be to get to a hiring fair. There, you can see and be seen, and show everyone you really have what it takes.
Good luck.

You're ticking many of the right boxes, and appear generally to be a good candidate. Your Achilles heel is your relative inexperience. Two years is short, any way you cut it. Focus on the medium level schools, or less-desirable locations, and you'll likely walk away with a job. And a few years down the road, if you continue to develop as you've started, you'll be in a position to move up.

One.

It sounds as if you're nearing the end of your overseas adventure. You had a dream, you lived it, enjoyed it, and now you're building a new dream. Don't beat yourself up. You're allowed to go home.
She of the petite bottom has given good advice. Check that this isn't a temporary issue brought on by stress, access your support network, make a decision and make a plan.
No need to panic, no need to break contract. Even if you have 1.75 years left before you return home (or just .75), just setting up an official end date might make a huge difference in how you're feeling.

Applying to two is ok, especially if you really have the quals for both. Applying to seven is desperate.
Write one cover letter addressing both positions, and really hit the nail on the head. In separate paragraphs, address each position, why you qualify, what you bring to the table, etc.
Otherwise, your cover letter needs to follow the same guidelines as any other cover letter.