I have a beater Raleigh that I have managed to keep for over 30 years. I paid a whopping $25 for it back in 1982. No real financial loss if got stolen, but I would pissed at it getting gone and even more pissed at having to walk 7+ miles home. I had the biggest baddest chain lock I could lay hands on at the time, when U-locks came on the market I added one of those to the arsenal. Depending on WHERE and for HOW LONG the bike was going to be locked up would determine my locking strategy. I use ring locks on a lot of my bikes now for the convenience but back them up with something more substantial if the bike is going to be left out of sight for a longer period of time.
Making the bike harder to steel that the bikes around it is a good strategy too.
Aaron