Replacing 5.7L head gasket

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1993 Chevrolet Caprice with 5.7L

It has a somewhat bad head gasket, which causes air to be thrown into the cooling system so that for the first 5 minutes of driving, the temperature gauge is in the red. This air prevents T-stat from opening. Then the t-stat opens and coolant starts circulating and is at normal temp for the rest of the trip. I am runnning a 195F T-stat, this doesn't happen with 160F.

Questions:

1) Does this mean the engine truly overheats in the first 5 minutes? Is it dangerous to drive for the first few minutes with gauge in the red? Or could the engine not overheat that quickly?

2) How hard would it be to replace the head gasket? I only need the driver's side, the other has been replaced.

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