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1) Is it sent from a business address or personal - business address or reshippers are their first clue that its taxable merchandise
2) Is your address business or personal (personal are more likely to have VAT applied as there is an exemption from VAT for registered businesses)
3) Has your address been flagged from past activity or high volume
4) Which local customs office and officer handles your parcel. In Munich there is one office in Garsching with only a few employees assessing the VAT. If you have been there before and were cordial they tend to be pretty accomodating.
5) If they have you open the package to view contents, they will look for obvious signs of it being new merchandise (packaging, tags, etc). This happened to me once for a leather bag I had reshipped to Germany. I had the reshipper remove all signs of purchase and the guys in Garching did not charge me VAT.
6) If it is obviously a new purchase then they may look at whether it is a brand that is recognized and available locally at higher prices. Never happened to me, but a friend here had to pay VAT on a price much higher than he actually paid because the item is sold locally for much more.
There may be more, but these I can attest to. In general there is much lower risk by having things sent from a non-commercial address with everything inside packed in a way to make it look not new and a personal note or letter from your friend. I have also seen success with claiming the item is being returned to its rightful owner either after being serviced or because it was left at a friend’s house when you visited: “repaired watch return to owner”, “fixed watch” or even “miscellaneous personal items”. If you do have to open it for customs, be cool and repectful and do not argue.