I narrowed it down to 6 watches, which seems to work for now. I recently sold a Flat 6 chronograph, which I thought I would miss, but not so much.
Gens:
Seiko 6309 Diver (weekend beater)
Debaufre Airforce (weekend)
Reps:
MBW 1680 red sub fully modded w/ gen 93150 bracelet (worn almost daily during the week)
MBW 1665 GWSD fully modded (fights w/ the 1680 for wrist time)
Swiss Yacht-Master w/ gen crown/tube (dress watch)
Omega SMP chronograph serviced w/ gen crown/tube and date wheel (usually worn at night during the week/weekend)