Tonguez
A suffusion of yellow
Dogs' sense of smell is hard for us humans to really comprehend. They can detect and discriminate scents that humans can't even notice and ten times the potency. It would be quite easy for a dog to pick out a scent from an item and then follow the person's scent through a city. There are some differences between ground and air-based scent dogs, but the most important factors are:
1. Obviously, if the scent is a week old, it's pretty much impossible (years and years ago, the record for a bloodhound successfully tracking a fugitive by scent was something like 4 or 5 days; that record might have been beaten, but probably not by much at all).
- How long has it been since the scent was left?
- What has the weather been like since then?
- What kind of item are the dogs using to acquire the scent?
- What kind of handlers do the dogs have?
- Are the prey trying to hide their scent tracks?
2. If it's been raining continuously for 12 hours, that's probably just as bad as dry weather for 4 or 5 days (and in a city, there can be all kind of things that have effects similar to weather).
As for the Rule of Cool, if the PCs are trying something new and creative, I would give them a reasonable chance of success if the scheme isn't too far-fetched.
Its important to remember that dogs following scent trails are Trailing scents and dander in the air NOT Tracking spoor on the ground.
2. the idea that rain is bad is actually not true, scent particles tend to be hydrophillic and the large particles Dander (skin fragments, sweat and saliva) are attracted to dampness. Rain actually helps to settle dander on the ground and that allows the dog to trail it better.
Dry windy weather is worse as it disperses scent over a greater area and thus means the dog needs to take longer to explore the trail. Thats where a skilled handler who understands how scent works helps, as they make judgement calls of patterns of dispersal and can direct the dogs into shaded areas where they are more likely to pick the trail up again.
Time and wind are the issue, but in a medieval city I think trained dogs with a skilled handler could find a recent trail easily enough.