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Should I be using a contrast filter?


A skylight is a weak UV filter.

A UV filter cuts down the amount of UV light that reaches the film. You cannot see UV light, but films do - some films more than others.

UV light tends to bounce around amongst the dust particles in our atmosphere (aka haze) so film sees more of the haze than our eyes do. A UV filter reduces that effect.

Try shots with and without the filter, on hazy days and days where the air is cleaner (like after a rain storm). You may very well see clear differences.
 
Try shots with and without the filter, on hazy days and days where the air is cleaner (like after a rain storm). You may very well see clear differences.

That is the best way, try them all and see what you get. Only then will you know.
 
For monochrome, a colour filter works to lighten matching parts of the subject and darkens other colours. You can preview the effect by flipping the filter in front of your eye and away. You should not need a filter to get a grey tone from blue sky unless you are underexposing or possibly over developing, or using Ortho film, for example.

With the exception of UV or Skylight 'clear lens caps', I put on a filter because I need the effect. Which means I have to change the way the film will render the scene to get the effect I want. i do a lot of landscape work, so I probably use yellow-green or green more than anything else to adjust the separation of foliage.
 
As stated above skylight and uv filters can help older lenses. The filters also cut the haze on distant objects. Take the same photographs with and without the filter and take good notes. You should see a difference for distance shots, you may see a difference on some of the rest. YMMV.
 
One year I was touring Nova Scotia and it rained for 10 days because of a hurricane stalled off the coast. The only thing that saved the day was a CC 10R filter which warmed up colors.