Lots of choices at that price point. Go to timezone.com for more research.
For new watches, I'd look at:
Baume & Mercier
For gently used watches, I'd consider:
Vintage watches will put you into a 14k/18k solid gold case and a nice classic look.
If you find a watch on a bracelet you like, you can always put it on an after market leather strap.
First, do your shirts fit properly? If so, then it sounds like you have something in your build or stance that makes OTR not right for you. Either find a best fit OTR and get extensive tailoring or go MTM or bespoke.
It's one variation called shoe shop lacing for a reason. I use straight bar lacing where you can't see the underside diagonals.
Lots of lacing styles here:
You are the groom? What does your fiancee suggest? Navy or charcoal seem to dark for a May FL wedding on a yacht. I would consider lighter colors (off-white, light blue, dove gray, etc.) to be more appropriate for the occasion.
As a rider and commuter, I would not wear wool dress pants on a bike if I had to look good when I arrived at the office (especially in Portland weather). Get all-weather bike pants (or full riding suit) and change when you get to the office.
Breitling chronograph to IWC portofino is a wide range in style. Best bang for the buck brands include: Tissot, Oris, Hamilton, Seiko, Sinn, Baume Mercier, Tutima. I suggest trying on as many as you can and find one you like. Buying sight unseen is not a good idea unless you know exactly what you want.