Been working in the watch industry for a year now and having developed a strong personal interest in timepiece, well, here's my take of what to look out for when getting your first luxury piece.
1. The Brand
Would you rather a more reputable brand, with proven track in terms of quality or if you prefer, a more niche/micro brand just to be a little different? Ideally, history of the watchmaker and the actual design of the watch should resonate with you. You can't deny the fact that being seen sporting some of the "household" names like Rolex will almost immediately communicate your "status" and "wealth" per se, instant gratification, ta dah!!! without even to explain your choice, such is not necessarily the case for some other brands in the same price bracket as Rolex.
In-House Movements v.s your typical ETA Movements, value is very subjective, as for ETA Movements, some see it as why would I pay thousands for a luxury piece with it's movement of relative low cost, commonly used, seen in other make and even in lower price bracket brands, modified or not, when taking only the "value" of the movement alone usually don't justify the cost discrepancy, okay let's face it, as with luxury products, prices are exorbitant, heavily marked up.
In-House Movements on the other hand, there is creativity, innovation, man hours involved in R&D, some of which you cannot put a price tag to, these are what makes In-House Movements more desirable that your typical "mass produced" standard ETA Movements.
That said, servicing an In-House Movement might be an issue, options are limited considering that you might have to send it back to the manufacture for servicing and that raises the question of access, to distributors and dealers in the region. On the other hand, ETA Movements can easily be serviced by any decent independent watchmaker.
Dress watches, divers, pilots, casual etc.
Assuming it's gonna be your daily beater, it really depends on what you do for a living, your attire, the nature of your job, you wouldn't want to be sporting a dressy piece in leather strap if your line of work requires you to be outdoors most of the time sweating it out.
Honestly tho, the intended purpose of a watch is to tell time, date can come in handy but anything more say chronographs may enhance the look, adding another dimension of complication to the movement, but, do you really use it? let alone need it.
It really boils down to whatever floats your boat for a luxury piece with the above points considered, or perhaps just for flaunting rights(oh come on! I'm sure some of you belong to this category! don't be shy!)? or rewarding yourself for reaching certain milestone?
Whatever the case, you must like it!
p.s watches, courtesy of a lovely group of friends whom through the passion for watches have we first got acquainted, only the Tudor Heritage Chrono belongs to me.