I have a strong and real fear that I might head down this path as well. So far been toeing the line. 

I assume this would be based on current state and not "going back in time" for the first watch or anything like that.

For me it would be a Nomos + Zelos (one of the many references, which might take a while to decide); or a Formex Reef. Not many watches I want sit squarely within that price range. They are either somewhat above, or somewhat below.

I feel there is a place for complications on the watch face as long as it fits the look; though more often than not, they just "make things worse" (I'm looking at you open heart - even though this isn't a complication per se).
 

I don't quite enjoy the GMT or pointer date - too many hands!

I do prefer the power reserve at the back for GS though. 

It helps to narrow it down, but the rules don't have to be "simple". I try not to have too much overlap, with some expections; e.g. very inexpensive watches like Seiko 5. So far been doing okay, but it means I need to thoroughly scout, because getting one watch means filling a slot for other watches of the same type.

It's a combination of factors. A few top factors for me would be aesthetic, movement, and points of differentiation (e.g. something which differentiates the watches from other watches).

There's no single factor for me that applies to every purchase or prospective purchase, but it usually has at least ONE of the points of consideration above being the main consideration.

There might be a few that I just don't seem to like at all right now. This might change as taste sometimes evolves in ways we don't expect, but here are a few of mine:
1. Breitling
2. Bell & Ross
3. Panerai
4. Tag Heuer

I try to care for them as much as reasonably possible. That means, I wear them out but take reasonable care not to get them dinged or scratched; but if it happens, it happens. I also wear a tougher watch (G-Shock) where I am out running heavy errands where I might be moving heavy bags/objects around and have a risk of snagging a strap onto shopping bags or other hazards.

So, yes I care, but no I'm not gonna limit my wearing because of it, and not going to cry over it.