As I seem to remember it, when the E-Type came out in Britain, it was selling for more or less £2280. When I bought my Fiat X1/9 in '98 I paid over £3000 for it and I then bough an Alfa at over £4000 about two years later. Inflation destroys all relative values, and collectability makes it far, far worse!
Sadly, XKEs were always beyond my means and I wouldn't dream of buying stuff like that used. I bought one used car, a Fiat 127 that had seen less than a year of previous ownership, and we had it in the UK for a couple of years to use on return trips there. My son 'looked after it' but in the event, the insurance was far too high when I had to transfer the thing's registration area to city-centre Glasgow instead of rural Perthshire which, for a while was legally accurate and much less expensive. As I was picking up all the bills, it had to go.
I see the reasons for city insurance being high: on one return trip I discovered the boot prints on the roof. Ironically, I live on a small island now where not much happens, but insurance is sky-high because, the company tells me, of foreign tourists driving hire cars. My Fiesta costs me just under 500 euros a year. I think that's pretty steep for what it is, and an average of perhaps three kilometres a day...
Rob C