It depends on the location, the softwood and the paint.
Location includes detailing to ensure that rainwater can run off and there are no little places where puddles of water can hang around. Since more days are dry than wet, good design of the detailing ensures that the wood is usully dry and when it does get wet it soon has a chance to dry out again. When dry most softwoods will last a long time.
Some softwoods are much more durable than others. (This usually applies only to the heart wood, not the sapwood.) Good ones are Douglas fir, larch and western red cedar. Scotts pine is pretty good too. These are losely described as 'redwood'. Other softwoods such as sitka spruce, known as 'whitewood' is best kept indoors as it is not very durable.
Paint. This is the real killer. Modern paints form a waterproof layer like a polythene bag. When a crack develops in the paint layer and water gets in it can't dry out again. The wood stays wet and then rots. Unpainted wood often lasts longer than painted wood as unpainted it can dry out. If you are going to paint it, use a really breathable paint such as the real linseed oil paint made in Sweden and sold by Holkham Paints or the German Aglaia paints sold by Womersleys amongs others.
Of course oak is a different story. Do you want your work to last half a millenium?
Just a word of warning about this terminology - if you tell a builder's merchant or timber yard that you want to buy "redwood", you'll invariably get pine (pinus sylvestris) not Doug Fir, larch or cedar. To be sure you get what you want, specify the exact variety you want.
That depends where you buy it. I paid £7.50 (ex-VAT) per cubic foot for Douglas fir a few weeks ago. It was bought, freshly felled and milled to my dimensions and delivered, from a forestry estate nearby.
Too late - it's now rafters holding up a roof. Actually Douglas fir is fairly dimensionally stable and the whole thing is a green build anyway. It can dry out in situ.