March 2001 for tax increase, or it was when I bought mine.
You can get late 2000 models that are facelift editions that get you into the lower tax band, one of the reasons I bought mine, it was registered in Nov 2000 but it's a facelift car, the accepted rule is facelift is from 2001- onwards but you do get some earlier examples like me if you're lucky.
As for insurance no idea, but I had mine insured through my Mrs and I renewed it last week, fully comp on a regular policy for 268 for the year They're only expensive to put fuel in and tyres on (245/40/18 Front & 275/35/18 Rear), the rest is reasonable.