How do I go about saving ALL data on an imac running 10.5.8 and wipe the harddrive and install an new OSX

I have an old imac running OSX 10.5.8 which for various reasons was never updated further
Processor is 2.4GHz Intel Core 2 Duo
memory 2 GB 667 MHz DDR2 SDRAM
It has iphoto 08 7.1.5 (378)
I also have a macbook Pro. Running OSX 10.7.5
Processor 2.4 GHz intelCore i5
memory 4GB 1333 Mhz DDR3
This one runs iphoto 11 v 9.2.3 (629.52)
On Both these Machines I want to save all the files and particularly the photos to an external hard drive. I can do the files etc but having problems with iphoto. I want a complete functional copy of both libraries in iphoto and I want to be able to access it and pick and choose which ones I want to use but not STORE on a new Macbook. I want to access the photos from several machines and just browse through them.
Then .. once I have a proper copy of everything I want to reformat the old imac and install the newest OSX it will run given its Processor etc. any advice on which OSX it can cope with?
Also possibly upgrade the macbook pro , so that they talk to each other properly, will access icloud and will also both be compatible with a new macbook pro running Yosimite...
But I want to be able to pick and choose which files I move to the new macbook. Both photos and general filing.
This may be easy for an expert but I am not an expert, I am reasonably competent.. but definitely not an expert and I don't want to mess up and lose stuff.
can anyone help?

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