What would you do?

Let's say you were a moderately obsessive watch collector, with a focus on 1960s and 1970s sport and dive watches, and you have a decent, mid-price range (collection +/- $5,000 to $15,000 pieces) mostly Rolex and Omega, but a couple of icons from Heuer, Movado, Zenith, and Doxa. You were thinking about picking up a Daytona, or maybe a 1655, but are open to suggestions. Budget is around $25,000. You want to buy something you like and can wear (carefully), but would want something that will probably increase in value over time.

So, what would you do?

Lots of variables at play here. If you give some more guidance maybe we can make useful responses.

I'm curious about where this is going too...

I don't think a manual wind Daytona can be had for $25k. I'd personally go for a 1665.

I think you would be less happy with a watch worth around 25k which you stated that you would wear "carefully." Over the years I've found that I grow more detached from a watch that I babied too much. I think it's better to have a variety of watches that are appreciating over time instead of one watch that you have to limit in terms of occasions to wear them.

Thanks everyone. I will try to respond to some of your posts here.

DarlinBoy - thank you for repeating my post. Hopefully that was intended as humor, but it's a bit hard to tell.

Watchlovr - A useful response. I have an Ed White, and the 2998 is pretty similar. Maybe a swap plus cash for the right example.

Calalum - Leaving it pretty wide open was kind of the point. I was hoping to hear what other enthusiasts thought with the limited information I provided.

Gminnj - Where this is going to (presumably not "too") is getting ideas on other watches to consider from knowledgeable watch enthusiasts based on the parameters in my email. Your input is surely welcome.

Overgrower - Older Daytona is tough on that budget, but maybe a 6262 or 6239 if I stretch? 1665 is a definite maybe.

Kyle - Big help dude!

Interstellar - Good point. So, what multiple pieces do you recommend on my budget. Be creative!

Foo2Rama - Good observations, but trying to stay Vintage.

This is going to be extremely biased for me Tennos, but honestly for 25k you can pick up a UG compax - Nina. I've seen a few on Chrono24 for 16k.

The reason for my suggestion is that I personally love the watch, but you yourself mentioned that your collection comprises mostly of sports and dive watches fromt he 60's and 70's.

I think the market for UG will be quite lucrative if you want to stray far from Omega and Rolex. Unlike Omega and Rolex, the quantity is not increasing.

Heuer Autavias are beautiful pieces you might want to consider, they'll definitely increase in price over time if you're more interested in chronographs. Reference 2446C and 2446C SN are nice ones.

However, I think the return on multiple watches will over time be more beneficial then just one watch. Not to mention the liability and stress from the pressure of rocking something that's 25k without enjoying it freely.

Very good suggestion on the Evil Nina. I have a 2446c. I'll keep my eye out. Good ones come up every now and again. Thanks