Hi Corzair, here are some steps for a different watch body strategy.

To start with, I drew this curve in the top view - I drew the curve on the right side first, the mirrored that around the origin, and then drew 2 lines for the top and bottom parts and joined all those together:



Then I switched to the right side and drew another profile and joined those 4 segments together:



You can now construct an object from these 2 profiles using Boolean Intersection. The boolean tools know how to automatically extrude out planar curves, so it isn't actually necessary to do the extrude yourself, just select the top curve, run Construct / Boolean / Isect, then select the side profile and push Done, that will give you this object:



Selecting that and filleting edges gives this:



Anyway, you can play around with the shapes to tune the result, I hope this gives you an idea of a different approach. It's generally kind of a good idea to sort of more block out a shape first and then fillet stuff to round edges later, rather than trying to loft it all in one single go.

- Michael