I work in a dealership, so I guess the neccesary tools are readily at hand. It would seem difficult to me to try to remove the fan without the proper tools. Also the guide rail pin puller as Benzmac already commented on. You also need to be careful when removing the head to not bust the rail itself (the guide rail sticks above the level of the timing cover).
On the belt tightener shock, sometimes you can tell when it really needs to be replaced. If the engine has a loose belt, it's not due to the shock, though. Probably the tightener is worn out. I usually replace the shock if one of the aluminum inserts on the end can be pushed out by hand, but yes, sometimes it's obvious by the noise that the shock is bad.
At this many miles, it may not be a bad idea to replace the timing chain. I guess it depends on what you want to do with the car, as replacing the chain adds quite a bit to the labor bill. If you want to drive it another 200K+ miles, then do it. I would also be looking at new valve guides, make sure this is included in the machine shop estimate.
You wouldn't need to R&R the radiator for this work. If you have problems getting the fan off, you may just end up removing the radiator and condensor to drill out the bolt, so be careful!