The advantage to owning a Rolex or other expensive watch is it can be sold and some money recouped. If you buy a $10,000 Rolex you can expect to be able to sell it quickly and get back 40%-50% of what you paid. I don't know how easy it would be to sell a cheap $200 watch.
The downside is expensive automatic watches require service every 3-5 years, and service can range from $400 to $1000+ depending on what watch.
Do your research before you buy, how much you can sell it used if you wanted to buy a different watch, how much it costs to service, ect.
You will be wearing the watch so buy what you like. Decide if a 36mm or 40mm or larger watch looks good on your wrist. Bigger is not always better, Charlie Sheen wears a 36mm YM on tv and he has a collection worth millions. Decide if you want steel, gold, white gold, or something else and be prepared to pay more than the precious metal is worth. Decide how much you want to spend. Decide what you will use the watch for, do you dive or swim with it, do you use it to time a race, do you want to know the day or date or other information on the watch? That should help make a decision.
I had a Rolex and sold it. It ran fast and I got tired of resetting the time every week. They offered to fix it, and perform a service for $1000. I sold it.
I have worn Omega but never owned one. Omega is pursuing Rolex to grab the market of $10,000 watches. They raise prices often to try and catch Rolex and they stopped selling in stores and now sell in corporate owned botiques. 5 years ago you could by a Seamaster for $2,000, now they are selling for triple that amount. Omega is developing in house movements. If you buy Omega, know what you're buying, if the movement is the more valuable inhouse or if it is an older movement, and if it is an older quartz that does not hold value like automatics.
What I like recently is the Citizen eco-drive watches. They are quartzs, they have almost no resale value, but they look good and they have features that I like.
Once you own and sell watches, you will probably want to have 2 or 3 nice watches.
Remember, if you own an automatic and don't wear it for a couple days it will stop running and you will have to reset the date, time, ect. They sell winder boxes to take care of that but some people think that reduces the life of a watch.
I hope you find a watch you like and don't worry too much about other people. I can say when I had my gold Rolex the only women who noticed it are women who had no good intentions than to try and get as much money from the wearer as possible. Most people didn't notice it. A cheap stylish watch may have more desired outcomes of completing a look you're going for without attracting attention from gold diggers.
I agree with most of your points except for the first one. That is possibly the worse reason to buy an expensive watch. If im gonna drop 5-30k for a watch im not thinking to myself "hey its ok cuz i can sell it for at least half the price later on!"