Trading it in, isn't going to help. The 1299 is even more extreme and fragile than the 1199. The 1199 was mostly vendor problems common to any brand new fresh slate machine.
Oil leak is an easy fix. Valve cover gasket most likely. Engines under race levels of internal vacuum have these issues.
Gear sensor is also an easy fix (if you get an up to date service tech). The 1299 has the exact same problem. Park the bike in first gear every night, NOT NEUTRAL. Why, I don't know,, but it's helped many.
I think it's a calibration thing when the ECM boots up. A minor bug. The sensor can also be recalibrated by the tech. I think it's a btch to replace, but most of the ones that were replaced, didn't need replacement.
IMO, these should be warranty items, even if the bike is out of warranty. They would be if it was my gig. Or I'd try sticking the repairs on a vin# that was under warranty still. Should be small potatos cost if they can't get warranty.