You can't mess the system up by bleeding it with brake fluid, so there won't be anything to regret. You might have to bleed it a lot though. You can't really dump any harsh cleaners in the system or you'll cause more problems than you'll fix. If the entire system is too far gone it will have to be replaced or the respective part renewed. That is just how brakes are done.
You can tell the system is good once you're done and it is sealed again. If it's bad you'll have a leak and little or no pressure at the lever. The lever, like the brake pedal in your car, should be firm and provide resistance at the end of its travel when the brakes are engaged.