If you want to wear the watch daily, then for practical reasons vintage might not be the right option for you. If investment is your primary motivation, then anything with a moonphase or minute repeater complication will continue to not only hold its value but appreciate. For a first purchase I would suggest choosing something simple and classic like a Calatrava. You can enjoy a beautiful timepiece and allow its value to appreciate, whilst building your knowledge. As your knowledge and confidence grows, you then have a model that you can either trade in for something more ambitious – or that can form the base of an expanding collection as you become more adventurous.