RE: When is it okay to go bigger?
It all depends on what you want to do with it, and what kind of plane you want. I had a bad experience with Dietrich/TopDawg. Aeroworks is heavy (read other threads, you'll see it's more than just me saying it) but if you don't feel like you'll EVER want to give a hard elevator input of any kind (like recovering from an ugly snap) then they'll be just fine (but still not worth the cost, to me). Extreme Flight is really nice, but they're a little costly. 3DHobby Shop really is nice, but they're a little costly. Peakmodels is cheaper and I've heard good things, hardware isn't the best...but it's mostly usable. Pilot-RC are good planes that are an up-and-coming company...I've heard good things. I can't think of other planes, but that should give you a good start of what to look at....but if you're just doing sport flying, pick the plane that you like the look of. I prefer Edges because of their 3D capabilities, but Extras fly smoother but don't 3D as well. Yaks fly a little smoother than Edges, and 3D better than Extras...kind of a 'tweener plane.
On set-up, go for what you can afford. I'd get one of 3 motors: MT70, DA60, DLE55 (in no particular order). Servos, I'd get an 8611/7955 for the rudder and then 8411's or PowerHD servos on ail and ele. Of course, metal arms (I like MPI) all around. Any standard servo will work on throttle. You can get a choke servo OR run a manual choke arm. I like the manual choke arm, less issues. In fact, my choke servo gave me FITS and would simply refuse to work. Caused a premature plug fouling and caused me to lose my engine mid-flight. Battery: depends on your charger. I like A123 and you can get an A123 compatible charger from Hobbyking for $30. Your ignition battery should be either 800mAh nimh pack or a lipo/reg. I have a lipo/reg just because I had it around the house (and you get more capacity per weight). You could also get an IBEF or Zeus instead. You'll need a kill switch for sure. Switches: you'll need a nice switch on your Rx. MPI has fail-on switches with built-in charge jacks. Fromeco Badgers/Wolverines are pretty fail-on switches with built-in charge jacks (I have a badger). The EMS switches on Tower are nice, too. Forget about a power expander, there's no need. Two receiver batteries might be worth it to you since you're doing sport flying, but I've got 1. You don't need 2 receivers...there's just no point. There are lots of pretty fuel dots out there. I like a 3-line setup with the fill line copper either curling under itself onto the bottom/front of the tank or just barely peaking through the stopper (that way you put the plane on its nose and can get all the fuel out. Remember to use lots of Loctite and loop your vent line over your tank and then run it out the bottom. Besides that, it's just a big ARF.