1. I differ from DMcQuinn in that you should check your battery EVERY flight. Just because in normal conditions you can easily get 3 flights from a fully charged battery stuff happens, didn't charge all the way, lost a cell after the first flight ect....
There is hot debate on the use of Voltwatch onboard battery monitors, I use them and they serve their purpose. Expanded scale voltmeter is more accurate but you have to remember to use it.
2. Cycling is not as important as it used to be but can rejuvinate a battery that is starting to lose some capacity. I use an Accu-Cyle charger that charges/ cycles both transmitter and receiver batteries But you can't discharge most transmitter batteries without removing the battery because of a diode in the transmitter.The Accu-Cycle I use is $63 at Tower Hobbies
http://www3.towerhobbies.com/cgi-bin...&I=LXL357&P=ML
3. Field charging is a personal choice. I put a 2,000mah battery in my transmitter and 1500 to 2000mah batteries in my airplanes. I charge at home and can fly all weekend without re-charging. I do have a good field charger just because I needed a good lipo charger. It is a Bantam E-station BC5. The BC5 was $125 but again I bought it for its ability to balance charge lipo batteries iy is just an added bonus that it will charge all my other batteries including my 12V gel-cell field box battery.
http://www.grandrc.com/inc/sdetail/66739