I replaced my left hand rad a couple of years back and found the job not very difficult. The front bumper as well as the wheel liners must be removed to get at the rad, fan, electrical and hoses. Having the front raised helps in minimizing coolant loss but at your milage and water pump issues you will likely replace all the fluid anyway. It is also likely at that age & milage that some of your hoses may need replacing as well. It is also a great time to clean all the crap from the rads and A/C rad.
There are a few videos out there showing the process and here are a couple covering 996 that is the same on the Boxster.
The biggest PITA are the clips that hold the radiator. They tend to corrode and are a pain to remove and replace. I replaced my right side radiator fan last year and it was about a 2 hour job.
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2004 Boxster S Silver - FUNTOY
2002 Boxster Base Guardsy Red - FUNBOX
1987 Caterham Super 7 1700 Supersprint
2009 Mercedes Benz CLK 350 convertible
1941 Dodge Luxury Liner Coupe
I would recommend while you are in there to clean out the leafs etc from the other side by pulling the AC out of the way if needed. I was told the main reason these rads develop leaks is because of dirt and leafs building up and holding moisture which leads to corrosion. Also I would test your fans before you even take it apart, or at least before you put it back together. They are 2 speed fans and it is common for the low speed to burn out. I am basing this info off my 2000 S, I assume it applies to yours as well.
FunToy
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