Bushcraft,
You are asking good questions.
Like bykfixer said, if you have a reliable charger you are good to go. Xtar makes reliable chargers, and HKJ tested this one and gave it a thumbs up!
LiIon batteries can be topped off without having to drain them. If kept at full charge they degrade a bit quicker, maybe you'll get three years instead of five years, but they are inexpensive enough.... who cares?
Your battery has over-discharge protection, and so does the light. You'll see it get dimmer, and it may even start to blink, at that point you NEED to recharge. But regardless you still can't damage the battery by running it too low because of the protection circuit.
Personally, I use both protected, and unprotected cells, and I do use a digital multi-meter to check the charge status of my cells to see if I need to charge them. I always want my lights ready to go, so if any of the cells in any of the lights is under 4.0 volts, I top it off.
Eventually, you'll get a digital multi meter, but you don't need to right away. Sometimes Harbor Freight gives them away for free. Otherwise they have them for about $6. You don't need anything fancy.
Depending upon how much you use it, you might top it off every night, like you do your cell phone, once a week, or every two weeks. You'll see what works for you.
I hope that you get to play with it tonight!