in the english language it has evolved from from something valuable (to you) to someone that you care for (so still has a high value to you) in some places like american english this new meaning has allmost entirely replaced the old meaning. In other places both are used. (I do believe it is used a lot in scotland the people i ve seen allways say dear instead of expensive)
Isle of Wight, if it's not too dear."
It would be sweet (lieve) in dear Chris. And someone is dear to me, i guess would become someone is important (belangrijk) to me or means a lot to me (betekend veel voor me) or I care (a lot) for (geef (veel) om)
The hardest one for me was plunder/fire. Here in America, "sack" is very rarely used to describe anything other then, say, a successful medieval siege. I have heard it in English (UK) language before but took a long time for my brain to find that association.