My friend and I want to do a short cross country down to VNC, but we're going to take two planes since we're taking some friends with us. Would we be able to do a flight following for both and still fly together? I'd also assume since we're going into Class B airspace that they would have to separate us as well?
If you maintain "standard formation" (within 100' and 1 mile of each other) then ATC keeps you that way, and only lead squawks or does the talking to ATC. If at anytime you go non-standard, then #2 will have to squawk....generally 4000.
Word of caution though, I DO NOT recommend pilots that HAVEN'T been trained in formation flight to undertake this endeavor; it's VERY risky. There are specific items/procedures that those undertaking form flying, especially takeoffs and landings, MUST understand, both from a lead and wing perspective. These items MUST be briefed and clear prior to stepping to the aircraft.
Items such as when taking the runway for departure, where does the leader place the wingman and why? What procedures should be followed in the event of lead/wing needing to abort prior to, or during, takeoff roll? What formation references does the wingman use to remain in position? Why is the runway centerline considered a "brick wall" and what happens if either aircraft violates said wall? For form flying: What are Lead/Wing ATC responsibilities for different phases/types of form flight? What are lead/wing responsibilities for effecting rejoins? What are the clues for detecting an overshoot? What are the procedures for performing an overshoot? In formation flying, things can go to hell in a handbasket obviously, or insidiously; and you have to be able to detect and react to both properly.
All that being said, with the proper training, formation flying can be fun and interesting; but I'll never fly formation with someone without the training (unless, of course, I'm instructing them in it). I do get somewhat leery reading AIM Section 7-5-10 covering Emergency Airborne Inspection of Other Aircraft. Again, a VERY risky maneuver. Some of you may remember the death of Senator John Heinz in 1991. He was riding as a pax in a Piper Aerostar that had an unsafe gear indication. A Bell 412 helo rejoined on the Aerostar, per the Aerostar pilot's request to check out the gear. The two aircraft ended up having a mid-air resulting in all fatal on both aircraft. Both crews were untrained in formation ops, and it bit them hard. There's very few situations where civilian aircraft HAVE to fly formation, and a word of caution, if any accident/incident arises from formation flight,
especially with an untrained crew, the FAA will have a field day invoking 14 CFR 91.13, Careless and Reckless Operation. Another midair that happened back in 1985 when I was in training (which I remember since it was big news) happened north of PHX near Camp Verde, AZ, and is linked here:
http://www.ntsb.gov/ntsb/brief.asp?ev_id=20001214X36208&key=2
For the questions you're asking, esp as to how formation flight relates to ATC, it's clear the training isn't there. Not a hit on you; because you can't be expected to know what you haven't been trained on.