SsZERO,
Indeed alot of questions so I will answer them with short replies:

1) Heli - The Caliber is not the best recommendation for scale use. I assume that is what you are referring to unless you are using the term "scalablitly" to mean growth potential. If that is what you mean then there are ALOT of good choices in that regard. For the $ the Hawk Sport is the winner hands down.

2)Tools - These are must haves when building: blade balancer, pitch guage, ball link pliers, hex wrenches, various glues, metric ruler, screwdrivers(phillips #1, #2).

3)Field Box - Tri Flow oil, starter, glow igniter, start wand, fuel pump, fuel, glow plugs, tools, battery voltage checker, etc.

4) Upgrades - If you are buying a quality kit for a beginner then you won't need any. The name of the game when beginning is keep it simple and cheap. No need for fiberglass or carbon blades and a bunch of CNC aluminum upgrades. Just buy fuel and burn it!! If you are buying a heli that people are recommending a bunch of upgrades for then you are getting the wrong heli. The only exception to this is for items like more bearings. But, even this is necessary for a brand new heli. Replace them when they wear out or your flight skills overstress them!

5) Radio - The 9C is a great choice as far as value goes. But, I think you should try to find someone with one and hold it. As a beginner comfort is everything and this radio is NOT very comfortable if you fly with index finger and thumb controlling the gimbals. If you want to fly thumbs the it's no problem. But, for me and a couple of my students we all have had problems with this. If you want a top end 8-9 channel PCM system then get the JR 8103. Even the Airtronics RD6000 is easier to handle. This is all opinion but you should hold all three of these if you can! As far as PCM goes get it!!! Do it now and you won't have to worry about it later. If you want to know why then send me some mail and I will give you the reasons. But, they are for the most part communication rate, glitch resistance, fail-safe.

6) Motor - If you are in the US and can get 15% nitro then go with a one-piece "tuned muffler". Tuned pipes are much to difficult on helis for a beginner. It's not the same thing as 1/8th scale buggies here. Just get a TT .39 with Ace upgrade muffler or the Century Speed Torpedo. You get alot more power out of the TT .39. The OS is known to be reliable but this new motor from TT is proving to be just as reliable but with alot more power.

7) Air filters - Helis don't stay around on the ground like cars/ buggies. We don't use air intakes cause if they fall of in flight usually the will change the fuel mixture and cause a flame out which could cost you alot more than that little $4.00 filter.

8) Flying - Get a sim!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!

As far as Caliber goes is there any specific reason you are considering this? Reason I ask is because for the $ it's a good choice but there are better. I have alot of experience with the latest offering in the 30 size. I might be able to help you find the best fit.