First and foremost, I like to wear what I own, but also keep it in good working order. I know servicing is expensive, especially at the higher end. So, I would want to keep a rotation of about 5 to 6 watches that I wear very regularly, including my dress pieces. That way, they can all reasonably be allocated a service and maintenance budget (i.e., for straps, etc.) but also can be enjoyed. I think that enjoyment is paramount for me; having a piece collecting dust is one of the few things I would hate to see happen.
Second, a good chunk of my life is active (for how long, we will see). Having watches that are nice but can tolerate water and land activity alike is pretty important to me; dress watches are meant for what I would call "limited use cases" and so I wouldn't be able to wear them as much. I would wear them in the city, at work, and so on—but I like to have multirole watches since I also don't dress up regularly. I won't pretend that I'm some explorer or anything, but I get out and about in bad weather/cold/remote places a fair amount. As counterintuitive as it might seem, I'd wear a Day-Date doing just about anything, shy of what would be unsafe for a mechanical watch (that's why I have a G-Shock

). At the least, this creates very cool memories for me.
Third, I'm really picky. So I've been trying hard to refine my tastes for the dress piece(s) I intend to own so that I'll be happy with them. That's why the GO SC and MG stand out; they're so incredibly special in different ways, and by all accounts have superlative elements in their own right. GO's mechanics are very impressive, which is why I'd pick that; MG's finishing and quality is, I hear, among the best in the industry (cf. Tim Mosso). Hence, I'd like to make a choice or two that I'm happy to stick with, because I've realized I really hate selling things.
Hopefully these make sense. I've tried to really think out my priorities and strategy since my budget isn't unlimited and neither is my time—trying to make the most of it, you could say.