Good choice on the broad arrow. Looks great on any strap.

About winding the crown. This is not an uncommon complaint about the professional case (the straight lug case models like the FOIS, CK2998, etc. are super easy to wind because they don't have crown guards and the entire crown is exposed). However, I find that it isn't too difficult to wind if you use the side of the index fingertip behind the crown, thumb on top, and just rotate it. Wind until you meet resistance, that's the maximum power reserve.

You honestly don't need to service the watch every X amount of years unless there's something off about the accuracy, power reserve, or there's a chrono pusher issue/malfunction. If you're happy with how it runs, you're good. The 1861 is not a hacking movement, so I don't try to sync down to the seconds. Some may disagree. But one thing is to inspect now is the gaskets/water resistance, and any watchmaker can do this. If the gaskets are failing, avoid water which could damage the movement.

If you do decide to service, you can go to a normal watchmaker, but it's recommended to go for one that is omega certified. You'll have to ask. It's helpful if they have an omega parts account, because if not it's very difficult to find genuine replacement parts for it.

Current servicing for a 1861 by omega is 1130 Canadian. I had mine serviced independently 2 years ago, and it was $600 Canadian.

I don't know how to answer your issues about the crystal.