I have been more lucky than not when it comes to reselling my watches. My only suggestion is to do your due diligence and fully research the brand, the watch and the market for that item before making your decision to keep or flip your watch. There have been many time when I got excited about a watch and once I have worn it a few times the magic had worn off and it either gets stored away to be given to someone else who I believe would better appreciate it or it gets posted for sale. I'm more into Vintage Pieces than I am Contemporary Watches, so for me it's easier to do my due diligence before I pull the trigger on a new purchase. Again, I've been very lucky in 90% of my flips. The others that I lost money on were all impulse buys that I regretted later.

GOOD LUCK.