The thought that immediately occurred to me was that if I were starting over again, even with the full knowledge that I have today, there are a number of pieces that I've owned that I would buy again. For me it's a matter of a journey -- one's development as a watch lover and collector.
For instance, I have owned (and sold) an Omega Speedy, a PP Aquanaut and 5015, and a Reverso Duo, and still own a JLC Memovox, a UN Monopusher chrono, a JLC Ultra-thin, and so on. Some of these are watches that I think "everyone should own" at some point, just to have the experience (for instance, the Speedy and a simple Reverso), and all of them are pieces that at the time purchased made a lot of sense -- but it's possible that as one develops over time, it gets to be time to move on to other things.
For me, I'm actually in the starting phases of such a transition. I looked for a long time for a piece that I could use as a simple daily wearer for both business and pleasure (and landed -- yesterday! -- on a VC Overseas Chrono), and now plan to sell off the majority of my less expensive watches in order to help fund the purchase of a small number of more precious pieces.
But my point is that if I hadn't owned a Memovox, for instance, and were starting out again today, I'd still want to own a Memovox at some point.
If I get to start from today and keep all of my experiences intact, would I sell my current collection and start over? Yes and no -- I would do the liquidation of part of my set of watches as described above, but I have a core set of "keepers" from both major brands and independents that I plan to keep for as long as I can.
If I were forced to sell the whole shooting match and start again, still with all experiences intact, the struggle (as usual) would be between "going big" with one landmark piece and buying what would be the first of a planned sequence of acquisitions. Going big would be something like a Duality, KV decimal repeater, or VC skeleton repeater. The portfolio play would definitely start with an Observatoire, and then there would be some other pieces in the mix including a VH Antiqua, FPJ Vagabondage, a Simplicity, and so on -- as well as re-acquisition of some of my faves from my current batch (over and above the Observatoire) including the AP EOT and Reverso repeater.
Enough from me!
Best,
Gary G