Well over two weeks of a family's income. Most people might get a couple new outfits a year. Your two outfits might actually be a substantial part of the income you receive from your employer, since they tended to pay in food, clothes, beer, etc.
Not necessary: because a cloaca is mostly hidden by scales. However if your story requires the use of some type of clothing, think along the lines of a Chinese finger trap: something that in normal use would tightly cling to the body, but by removing in the opposite direction of slithering would be generally easy.
You don't mention if your creature has upper limbs or not.
If it has no upper limbs, the only option seems to be to have a sort of sleeve with something clingy on their body, either by using a belt in an area not in contact with the ground or by using elastic fabric that fits snug.
If they have upper limbs, on top of the solutions mentioned above they can ...