Okay.. since Greebo's sharing his trade's secrets

Let me add a few of my own. I usually weather stuff as Greebo does, so I'll just add in a few things to his excellent tips.
1. Weathering differs upon aircraft, and the state and quality of their maintenance. So, to do good weathering, it helps to know the history of the plane you are depicting.
For example, the Fw190A-5 of III./JG2, was Egon Meyer's plane. Meyer was the commander of the unit and a very prominent Ace, and it is natural to assume that the maintenance done to his plane would be generally in better qualuty than the other pilots.
So, the weathering would be slight, and the plane would generally look 'fresh' in those types of aircraft.

However, the Fw190A-5 of the SKG10 I did used a bit heavier weathering. The Luftwaffe still had a good quality of paint than compared to the Japanese, and its maintenance status would be still not too bad.

Notice the 'paint chipping' is heavier than Meyer's A-5, and is concentrated on the areas which would see most movement. Observe the 'line' of chipping following the canopy rails, since the 190 canopies would slide backwards to open. Also, the cowl areas would be constantly removed upon every maintenance inspection, so it requires a bit more chipping.
However, the more important weathering aspect for this plane would not be in paint chipping, but depicting the ground conditions of the airfields they operated from. Eastern front fighters first began operations in well paved fields, but as the war progressed and the territorial conditions changed, it was not uncommon for these fighters to move to more inferior fields with bad landing strips - often dusty, muddy, and exposed to bad weather.
Like Greebo explained, there is a certain 'logic' to how these dusty, muddy trails are left behind. Air is sucked by the props and pushed backwards alongside the fuselage. Undern Eastern Front conditions, the 'dust' would be generally reddish/brown soil. It leaves a marked trail of reddish brown alongside the under parts of the side fuselage, as can be noticed in the pic.
2. The way paints chip off, also has its own logic. On surfaces without any obstructions, the paint will chip off in any shape or size. However, when there are obstructions to the surface such as rivets or panel lines, the paints will start to chip off from one corner, and then follow the path of the obstructive surfaces.

Chipping usually starts at (A) where two panel lines are intersectioned. It progresses towards (B) and (C), but rarely towards the front end of the plane. Usually the chipping progesses towards the rear of the plane.
As the chipping progresses towards (B) it will become thinner and smaller, until it comes to (B) and meets a line of rivets. And then, the chipping will diverge, one line following the panel line, and the other line following the rivet line.
The worse the quality of paint, the heavier this tendency becomes - this tendency is especially noticieable in Japaneses planes.
3. Some 'obvious' features have a tendency which may be represented due to popular misconceptions. For instance, the exhaust smoke from the guns.
Many people portray the gun smoke trails too heavily. I use to do that too. It wasn't until sometime that people showed me a pic of how gun smoke trail was left in real planes, that I noticed there were certain mistakes.
Smoke trails starting from the barrel of the gun, which leaves a mark on the wings, is usually thin and defined. They are not spreaded out or thick. It is usually a thin line of smoke trail which doesn't fan out.
Where this smoke trail really 'fans out' and spreads, is the shell ejection port. Here, the smoke trail fans out towards the rear of the plane.
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Let me see if I can think up any more to be shared.