These are two great choices.Since the watch would be a daily and only one, I would want something that could take some abuse and still look good and continue to function over the years.
It would be between a used Sinn 856 Tegimented on Strap. The problem I would see is that since it has the copper sulphate capsule and inert gas, I am tied to having RGM here in the states for service. Not a huge negative but also not a positive. The Tegimented would help with scratches as the years pass by. The technology (there is more to list of course) would help delay the inevitable service.
The other choice would be the the Damasko DA38. The ice hardened would help with scratches and dings. The 2836-2 could be serviced by any competent watchmaker. And it could be purchased new with warranty for the allotted $1500 with change to spare. The savings could go towards straps or saved for the eventual service.
I struggled with this same question but with about half of your proposed budget. I landed on a microbrand: BOLDR. Specifically, the Expedition. It has a Sellita SW200-1 movement, dual screw-down crown, 200m water resistance, double dome sapphire crystal (with AR). It's a hybrid (field and diver) which strikes me as perfect for an everyday beater. All for about $600.If you can buy only one watch around $1500 for daily use and use it for the rest of your life,
what would you like to buy?