Welcome!
Are the games new user friendly, I dont know are you willing to introduce yourself to people?

The game is only as user friendly as you want to make it. Even stock TM aeg's do well in most games. If you are willing to come out and play we will make it fun for you

What format are the madcow games played in? Well generaly speaking they are small scenarios played out over a couple of hours like hold a location for x amount of time. Most airsoft games are like this, occasionally there will be a "miniOp" which is an all day event with lots of missions designed to challenge players. True Op's like Emerald Snow three are more advanced "miniOp's" in that they last longer, involve more players, and are more indepth. All of these games are based around pseudo Military simulation and/or police/mercenary style games.
Canfields is a good place to look at guns, they have some Classic army stuff there that hopefully will be ok to start with. They will be around the 300-350$ range and are GREAT starter guns (I doubt Canfields carries the latest fiasco's from Classic army but meh

) There is a good chance you will have a good solid working gun out of the box. I believe they also have some other accessories there? I dont know but you can ask the guys there at the paintball/airsoft counter.
Really honestly, all you need to play is Eye Protection and someone willing to loan/rent you a gun. Camo isnt essential but does help to make the game more indepth than just a backyard shout out

Pistols are over rated in my oppinion gas pistols can be unreliable in cold weather and in general are way to short ranged to be of any use short of an absolute last resort. I had one long ago and sold it since I never used it.
I would start with:
Good Solid Sealed Eye protection (say goggles)
Good pair of hiking boots or military boots (the later prefered as they have better ankle support)
Some old US Woodland BDU's
and some basic Rigging to hold AEG mags
A good starting AEG. I recommend CA line of guns (well I roughly suggest them

) for local investment. If you go online, ICS, G&P, CYMA, CA, JG, Echo1, and TM are all good guns to start off with(My preference is in order listed.
That is very basic and relativly cheap. That up there shouldnt be terribly expensive to start off with, something similiar to paintball starting off with (no more than 500$)