thinking out loud....

[supacharja]

Buying a Rolex is unlike "cash" in that there is invariably the j-curve effect. Once you buy the watch, you need to insure it and possibly service it if per-owned, hence the Rolex has a deflationary effect for a time unless bought at significant discount to market. And even if bought new, unless at a significant discount and out of state to avoid tax hit, after factoring in some wear and tear, it will take time to recoup your initial investment as someone won't buy from you for what you paid when they can likely buy brand new from a trusted seller with stickers, hangtag, new watch smell etc.

So, in my humble opinion, if you err on the side of caution, sell a few of your least favorite watches, which you will likely take a hit on if bought recently in exchange for funding the more important engagement ring. Then you have a wedding ring to consider, the wedding etc. I just got married and it was more expensive than I could have ever imagined. Way above budget, but the best money ever spent. Happy wife, happy life.

This is reality and anyone telling you cash and Rolex are lateral moves is dead wrong if you do the math (unless you can buy at dealer cost). And you can only sell in a flash if you sell one of your watches very reasonably. If not, factor in the time value of money.

Since you don't seem to have a stash of cash laying around that makes you feel more than comfortable, I would suggest you consider cash to be king for you at this stage. The watches will always be there in the future. My 2c. Wishing you and yours a healthy and happy life.