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I'm not the best painter in the world, but here goes.
The answer is really what works best for you. Simple as that.
If you look at the work of the guys on hear you will see that some ie Pat Johnson assemble everthing including stowage and then paint it in situ. Other paint it seperatley and then add after the main paint work but before weathering.
I suggest you look at the in progress pics of the guys here and look how they do there stowage. Then practice useing some old kits.
There are also some books which show how to do things. The Osprey modelling series is good ie Steve Zaloga etc. Check the Osprey web site. Im sure there are u tube step by step gudies as well, but I have not looked.
One idea i have found is
Soft items like canvas, bedding rolls, webbing items are difficult to get the right look as they are soft. So sometimes its best to add these before painting to avoid gaps and that added hard plastic look. Some guys cover the model in cling film ( clear cooking film ). Then add all the stowage using model putty etc ( Not glue, it melts the cling film). The cling film allows the stowage to follow the shape of the tank but stops it sicking to the tank.Once all stowage is palced and fully dry, remove. Then paint the stowage seperatley and glue back on when tank painted. Hope this makes sense as difficult to describe in words !!!
But do general weathering ie dust, mud etc WITH stowage on the tank as it blends the items together.
Generaly I used a combination of all all 3 style, add on before paint, add on after and the above. There no hard and fast rules.