Be very careful if the mix position is off axis. On axis, you will experience a "coupling" of the sub speakers. Off axis, you will be wanting to add a lot of low end which will kill your mix on axis.
Ideally, the lead sound tech is quite aware of this problem and splayed to sub boxes to fill up the low end in the whole are that people will be listening in. But, I have found that just because the lead sound tech has the job, doesn't mean he has ANY clue about how to properly splay speakers to create a balanced sound in the whole audience area. It is up to YOU to get there early and walk around the place to hear how it sounds different in different areas and compare that to how it sounds at the mix position. In outdoor gigs, mix position almost always sounds very different the even 20' either side of it, and certainly up closer will sound much different too.
Indoor venues in the 400-500 capacity range will usually have a natural RT time of around 1-1.4 seconds. Outdoors, you will have NO RT time at all!!! This can really mess you up if you are not used to it because everything is going to sound very dull and direct. One way around this is to make sure that you don't get your mics too close to things like drums and guitar cabinets. Pull them away an extra couple of inches from where you would normally mic them at and the sound will not be so direct coming out of the mains. Be prepared to hear digital reverb (if you use it) to sound EXACTLY the way it sounds, rather than how it sounds blended with a natural RT time in a room. You might find that you will need to really tweek the eq on the verb to make it sound like an ambiant effect. Try not to over do it though....
As far as sound checking through headphones. Well, welcome to the big leagues friend!!!

Basically, you will probably use half the eq you would use on the any given channel indoors, so, when you are line checking instruments, keep that in mind. Basically, your line check is just to get some preamp levels set and optimized before the band starts playing. If you are good at mixing live, you should have a decent enough mix in about a half a song. Remember that outdoors, any tweek you do on EQ will be far more noticable so take it slow in adjusting things in the first song, unless it is REALLY out of whack sounding....
Try not to sweat it too much. Outdoor mixing offer far more control, and you get to enjoy the sun at the same time....
Good luck.
Ed