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[holtender]

Imagining I had some real money to invest, any suggestions what I should be looking for???

[albitz]

Claptons Blackie Strat. Rory Gallaghers worn sunburst Strat (which has never come up for sale). Hendrix,s white Strat.The Gary Moore/ Peter Green Les Paul. Not necessarily in that order.
Clapton auctioned off hundreds of his guitars to raise funds for his Crossroads,substance dependency clinic,and some of those will change hands for reasonably sensible sums off money.

[albitz]

Claptons Blackie has now been surpassed apparently.
http://most-expensive.com/guitar-in-world

[Rog]

Imagining I had some real money to invest, any suggestions what I should be looking for???

Tell you what I'll sell you my '94 Strat for £250k. It's not worth it and has zero rock history, it but it could well become the most expensive. 

Oooops, just read the above. Price has now gone up to £3m. It's ok, you won't need to pay cash BACS will do 

[albitz]

Or buy my 2003 Strat for £500. I might become a rock legend one day (just after pigs have learnt to fly) and it will be a really good investment. Bargain.

[omega3000]

I should imagine Angus and Malcolm Young's guitars are worth a fair bit