From my personal experience, yes, charging systems will eventually fail. Your best bet is to check its performance now and monitor it moving forward. Here is the basic setup I have for a cheap volt gauge:
Run a simple two-wire cigarette lighter cable from the battery up to your dash
Stick a cheapo voltmeter ($5-10 on ebay) in there and you're good. Just pop it in when you go for a ride and you have peace of mind knowing that the system works. Of course, when you're not riding I would toss it in your bag. It doesn't draw much, but I never leave mine plugged in.
